Pyrrolidinyl-substituted para-phenylenediamine derivatives substituted with a cationic radical, and use of these derivatives for dyeing keratin fibres

ABSTRACT

Novel pyrrolidinyl-substituted para-phenylenediamine derivatives comprising a cationic radical, the dye compositions comprising them and the process for dyeing keratin fibers using these compositions, making it possible to obtain a chromatic, powerful, unselective and fast coloration of keratin fibers.

[0001] This application claims benefit of U.S. Provisional ApplicationNo. 60/387,499, filed Jun. 11, 2002.

[0002] The disclosure relates to novel pyrrolidinyl-substitutedpara-phenylenediamine derivatives comprising a cationic radical chosenfrom compounds of formula (I), as defined herein. This disclosure alsorelates to the dye compositions comprising them and the process fordyeing keratin fibers using these compositions.

[0003] It is well-known practice to dye keratin fibers, such as humanhair, with dye compositions comprising oxidation dye precursors, alsoknown as oxidation bases, such as ortho- or para-phenylenediamines,ortho- or para-aminophenols, heterocyclic compounds such asdiaminopyrazole derivatives, pyrazolo[1,5-a]pyrimidine derivatives,pyrimidine derivatives, pyridine derivatives, 5,6-dihydroxyindolederivatives and 5,6-dihydroxyindoline derivatives. Oxidation dyeprecursors, or oxidation bases, are colorless or weakly coloredcompounds that, when combined with oxidizing products, can give rise tocolored compounds and dyes by a process of oxidative condensation.

[0004] It is also known that the shades obtained with these oxidationbases may be varied by combining them with couplers or colorationmodifiers. These couplers or coloration modifiers may be chosen, forexample, from aromatic meta-diamines, meta-aminophenols,meta-hydroxyphenols and certain heterocyclic compounds such as, forexample, pyrazolo[1,5-b]-1,2,4-triazole derivatives,pyrazolo[3,2-c]-1,2,4-triazole derivatives, pyrazolo[1,5-a]pyrimidinederivatives, pyridine derivatives, pyrazol-5-one derivatives, indolinederivatives and indole derivatives.

[0005] The variety of molecules used as oxidation bases and couplersmake it possible to obtain a wide range of colors.

[0006] The “permanent” coloration obtained with these oxidation dyesshould moreover satisfy a number of requirements. For example, it shouldhave no toxicological drawbacks, it should allow shades to be obtainedin the desired intensity, and it should show good resistance to externalagents such as light, bad weather, washing, permanent-waving,perspiration and rubbing.

[0007] The oxidation dyes should also, for example, allow white hairs tobe covered. Further, the oxidation dyes should be as unselective aspossible, i.e., they should produce the smallest possible colordifferences along the same length of keratin fiber, which may bedifferently sensitized (i.e. damaged) between its end and its root. Theoxidation dyes should also, for example, show good chemical stability inthe formulations, and, further for example, have a good toxicologicalprofile.

[0008] In the field of hair dyeing, para-phenylenediamine andpara-tolylenediamine are oxidation bases that are widely used. Theseoxidation bases may, for example, provide varied shades when used withoxidation couplers.

[0009] However, there is a need to discover novel oxidation bases thatmay have a better toxicological profile than para-phenylenediamine andpara-tolylenediamine, while at the same time may give the hair at leastone of the following excellent properties: color intensity, variety ofshades, color uniformity and fastness with respect to external agents.

[0010] It is already known practice to use para-phenylenediaminederivatives substituted with a pyrrolidine group as oxidation bases fordyeing keratin fibers. For example, U.S. Pat. No. 5,851,237 disclosesthe use of 1-(4-aminophenyl)pyrrolidine derivatives optionallysubstituted on the benzene nucleus, to replace para-phenylenediamine.

[0011] U.S. Pat. No. 5,993,491 discloses the use ofN-(4-aminophenyl)-2-hydroxymethylpyrrolidine derivatives optionallysubstituted on the benzene nucleus and on the pyrrolidine heterocycle inposition 4 with a hydroxyl radical, in order to replacepara-phenylenediamine.

[0012] Japanese Patent Application 11-158 048 discloses compositionscontaining at least one compound chosen from 4-aminoaniline derivativesoptionally substituted on the benzene nucleus, and one of the nitrogenatoms of which is included in a 5- to 7-membered carbon ring.

[0013] It is established that these compounds may not make it possibleto give the hair a coloration that is equivalent in quality to thatobtained with para-phenylenediamine or with para-tolylenediamine due tothe lack of intensity and color uniformity.

[0014] There is thus a real need to discover novel oxidation bases thatmay, for example, have both a good toxicological profile and propertiessuch that the compositions comprising them may be able to give the hairat least one of the following excellent properties: color intensity,variety of shades, color uniformity and fastness with respect to thevarious attacking factors to which the hair may be subjected.

[0015] Disclosed herein are novel dye compositions that can overcome atleast one drawback of the oxidation bases of the prior art. For example,disclosed herein are novel dye compositions for dyeing keratin fibers,which do not degrade the keratin fibers, while at the same time arecapable of generating intense colorations in varied shades, and whichmay be unselective, resistant and can have a good toxicological profile.

[0016] Further disclosed herein is a compound chosen frompyrrolidinyl-substituted para-phenylenediamine derivatives of formula(I) and the addition salts thereof

[0017] wherein

[0018] n ranges from 0 to 4, wherein when n is greater than or equal to2, then the radicals R₁ may be identical or different,

[0019] R₁ is chosen from halogens; onium radicals Z; and C₁-C₆ aliphaticand alicyclic, saturated and unsaturated hydrocarbon-based chainswherein the hydrocarbon-based chains may be interrupted with at leastone entity chosen from oxygen, nitrogen, silicon, and sulphur atoms, anda SO₂ radical; with the proviso that the radical R₁ does not comprise aperoxide bond, a diazo radical, a nitro radical or a nitroso radical,

[0020] R₂ is chosen from onium radicals Z chosen from radicals offormulae (II), (III) and (IV), and radicals —X—C═NR₈—NR₉R₁₀, wherein Xis chosen from oxygen and —NR₁₁ radicals, and R₈, R₉, R₁₀ and R₁₁, whichmay be identical or different, are each chosen from hydrogen, C₁-C₄alkyl radicals and C₁-C₄ hydroxyalkyl radicals.

[0021] For example, R₁ may be chosen from a chlorine atom, and methyl,ethyl, isopropyl, vinyl, allyl, methoxymethyl, hydroxyethyl,1-carboxymethyl, 1-aminomethyl, 2-carboxyethyl, 2-hydroxyethyl,3-hydroxypropyl, 1,2-dihydroxyethyl, 1-hydroxy-2-aminoethyl,1-amino-2-hydroxyethyl, 1,2-diaminoethyl, methoxy, ethoxy, allyloxy and2-hydroxyethyloxy radicals.

[0022] Further disclosed herein is a dyeing composition comprising, in amedium suitable for dyeing keratin fibers, at least one oxidation basechosen from pyrrolidinyl-substituted para-phenylenediamine derivativesof formula (I) and the addition salts thereof.

[0023] Also disclosed herein is the use of this composition for dyeingkeratin fibers and the process for dyeing keratin fibers, for example,human keratin fibers such as hair, using the composition disclosedherein.

[0024] The composition disclosed herein may make it possible to obtain,for example, a chromatic, powerful, unselective and fast coloration ofkeratin fibers.

[0025] As used herein, an aliphatic hydrocarbon-based chain is chosenfrom linear and branched chains that may comprise at least oneunsaturation chosen from unsaturations of the alkene type and the alkynetype. An alicyclic hydrocarbon-based chain is chosen from saturated andunsaturated, linear and branched chains not containing an aromaticcyclic structure.

[0026] When the aliphatic hydrocarbon-based chain or the alicyclichydrocarbon-based chain is interrupted with an entity Y chosen from anoxygen atom, a sulphur atom, a nitrogen atom, a silicon atom and a SO₂radical, a unit CH₂—Y—CH₂ is obtained, for example.

[0027] The term “onium” means a nitrogen-based quaternary radical.

[0028] In formula (I), when n is equal to 1, R₁ may, for example, bechosen from halogen atoms; C₁-C₆ aliphatic and alicyclic, saturated andunsaturated hydrocarbon-based chains, at least one carbon atom possiblybeing replaced with an entity chosen from an oxygen atom, a nitrogenatom, a silicon atom, a sulphur atom, and a SO₂ radical, with theproviso that the radical R₁ does not comprise a peroxide bond, a diazoradical, a nitro radical or a nitroso radical. R₁ may also, for example,be chosen from chlorine, bromine and C₁-C₄ alkyl, C₁-C₄ hydroxyalkyl,C₁-C₄ aminoalkyl, C₁-C₄ alkoxy and C₁-C₄ hydroxyalkoxy radicals.Further, for example, R₁ may be chosen from methyl, hydroxymethyl,2-hydroxyethyl, 1,2-dihydroxyethyl, methoxy, isopropyloxy and2-hydroxyethoxy radicals.

[0029] The onium radicals Z may be chosen from radicals of formula (II)

[0030] wherein

[0031] D is a linking arm chosen from a covalent bond and linear andbranched C₁-C₁₄ alkylene chains which may be interrupted with at leastone hetero atom chosen from oxygen, sulphur and nitrogen, and which maybe substituted with at least one radical chosen from hydroxyl, C₁-C₆alkoxy and amino radicals, and which may bear at least one ketonefunctional group;

[0032] R₄, R₅ and R₆, which may be identical or different, takenseparately, are each chosen from C₁-C₁₅ alkyl radicals; C₁-C₆monohydroxyalkyl radicals; C₂-C₆ polyhydroxyalkyl radicals;(C₁-C₆)alkoxy(C₁-C₆)alkyl radicals; aryl radicals; benzyl radicals;C₁-C₆ amidoalkyl radicals; tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals;C₁-C₆ aminoalkyl radicals; and C₁-C₆ aminoalkyl radicals wherein theamine is mono or disubstituted with a radical or two radicals, which maybe identical or different, chosen from C₁-C₄ alkyl,(C₁-C₆)alkylcarbonyl, amido and (C₁-C₆)alkylsulphonyl radicals; with theproviso that when the linking arm D is a covalent bond then R₄ is chosenfrom aryl radicals; benzyl radicals; C₁-C₆ amidoalkyl radicals;tri(C₁-C₆)-alkylsilane(C₁-C₆)alkyl radicals; C₁-C₆ aminoalkyl radicals;C₁-C₆ aminoalkyl radicals wherein the amine is mono- or disubstitutedwith a radical or two radicals, which may be identical or different,chosen from C₁-C₄ alkyl, (C₁-C₆)alkylcarbonyl, amido and(C₁-C₆)alkylsulphonyl radicals,

[0033] Two of the radicals chosen from R₄, R₅ and R₆ form, together withthe nitrogen atom to which they are attached, a saturated carbon-basedcationic ring chosen from 4-, 5-, 6- and 7-membered rings optionallycomprising at least one hetero atom, for example, a cationic ring chosenfrom azetidine rings, pyrrolidine rings, piperidine rings, piperazinerings and morpholine rings, wherein the cationic ring may be substitutedwith at least one entity chosen from halogens, a hydroxyl radical, C₁-C₆alkyl radicals, C₁-C₆ monohydroxyalkyl radicals, C₂-C₆ polyhydroxyalkylradicals, C₁-C₆ alkoxy radicals, tri(C₁-C₆)alkylsilane(C₁-C₆)alkylradicals, amido radicals, carboxyl radicals, (C₁-C₆)alkylcarbonylradicals, thio (—SH) radicals, C₁-C₆ thioalkyl (—R—SH) radicals,(C₁-C₆)alkylthio radicals, amino radicals, and amino radicals mono-,di-, or tri- substituted with a radical or radicals, which may beidentical or different, chosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl,amido and (C₁-C₆)alkylsulphonyl radicals;

[0034] R₇ is chosen from C₁-C₆ alkyl radicals; C₁-C₆ monohydroxyalkylradicals; C₂-C₆ polyhydroxyalkyl radicals; aryl radicals; benzylradicals; C₁-C₆ aminoalkyl radicals; C₁-C₆ aminoalkyl radicals whereinthe amine may be mono- or disubstituted with a radical or two radicals,which may be identical or different, chosen from (C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl, amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆carboxyalkyl radicals; C₁-C₆ carbamylalkyl radicals; C₁-C₆trifluoroalkyl radicals; tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals;C₁-C₆ sulphonamidoalkyl radicals; (C₁-C₆)alkylcarboxy(C₁-C₆)alkylradicals; (C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radicals;N-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylsulphonamido(C₁-C₆)alkyl radicals;

[0035] x is 0 or 1,

[0036] when x=0, then the linking arm D is attached to the nitrogen atombearing the radicals R₄, R₅, and R₆,

[0037] when x=1, then two of the radicals chosen from R₄, R₅, and R₆form, together with the nitrogen atom to which they are attached, asaturated ring chosen from 4-, 5-, 6- and 7-membered rings and thelinking arm D is linked to a carbon atom of the saturated ring;

[0038] Y is a counter-ion.

[0039] In formula (II), when x is equal to 0, then R₄, R₅ and R₆, whichmay be identical or different, are each, for example, chosen from C₁-C₆alkyl radicals, C₁-C₄ monohydroxyalkyl radicals, C₂-C₄ polyhydroxyalkylradicals, (C₁-C₆)alkoxy(C₁-C₄)alkyl radicals, C₁-C₆ amidoalkyl radicals,tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, or R₄ and R₅ form, togetherwith the nitrogen to which they are attached, a ring chosen fromazetidine, pyrrolidine, piperidine, piperazine and morpholine rings, R₆being chosen in this case from C₁-C₆ alkyl radicals; C₁-C₆monohydroxyalkyl radicals; C₂-C₆ polyhydroxyalkyl radicals; C₁-C₆aminoalkyl radicals; C₁-C₆ aminoalkyl radicals wherein the amine may bemono- or disubstituted with a radical or two radicals, chosen from(C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl, amido and (C₁-C₆)alkylsulphonylradicals; C₁-C₆ carbamylalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals.

[0040] When x is equal to 1, then R₇ is, for example, chosen from C₁-C₆alkyl radicals; C₁-C₆ monohydroxyalkyl radicals; C₂-C₆ polyhydroxyalkylradicals; C₁-C₆ aminoalkyl radicals; C₁-C₆ aminoalkyl radicals whereinthe amine may be mono- or disubstituted with a radical or two radicals,which may be identical or different, chosen from (C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl, amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆carbamylalkyl radicals; tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals; R₄ and R₅ form, togetherwith the nitrogen to which they are attached, a ring chosen fromazetidine, pyrrolidine, piperidine, piperazine and morpholine rings, R₆being chosen in this case from C₁-C₆ alkyl radicals; C₁-C₆monohydroxyalkyl radicals; C₂-C₆ polyhydroxyalkyl radicals; C₁-C₆aminoalkyl radicals; C₁-C₆ aminoalkyl radicals wherein the amine may bemono- or disubstituted with a radical or two radicals, which may beidentical or different, chosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl,amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆ carbamylalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals.

[0041] In formula (II), the linking arm D may, for example, be chosenfrom a covalent bond and an alkylene chain that may be substituted.

[0042] The onium radicals Z may be chosen from radicals of formula (III)

[0043] wherein

[0044] D is a linking arm chosen from a covalent bond and linear andbranched C₁-C₁₄ alkylene chains that may be interrupted with at leastone hetero atom chosen from oxygen, sulphur and nitrogen, and that maybe substituted with at least one radical chosen from hydroxyl, C₁-C₆alkoxy and amino radicals, and that may bear at least one ketonefunctional group;

[0045] the ring members E, G, J and L, which may be identical ordifferent, are each chosen from carbon, oxygen, sulphur and nitrogenatoms to form, together with the ring nitrogen, a ring chosen frompyrrole, pyrazole, imidazole, triazole, oxazole, isoxazole, thiazole andisothiazole rings,

[0046] q is an integer ranging from 0 to 4;

[0047] o is an integer ranging from 0 to 3;

[0048] q+o is an integer ranging from 0 to 4;

[0049] R, which may be identical or different, is chosen from halogens,a hydroxyl radical, C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkylradicals, C₂-C₆ polyhydroxyalkyl radicals, C₁-C₆ alkoxy radicals,tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, amido radicals, carboxylradicals, C₁-C₆ alkylcarbonyl radicals, thio radicals, C₁-C₆ thioalkylradicals, (C₁-C₆)alkylthio radicals, amino radicals, amino radicalsmono- or disubstituted with a radical or two radicals, which may beidentical or different, chosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl,amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆ monohydroxyalkylradicals and C₂-C₆ polyhydroxyalkyl radicals; it being understood thatthe radical R is borne by a carbon atom,

[0050] R₃, which may be identical or different, is chosen from C₁-C₆alkyl radicals, C₁-C₆ monohydroxyalkyl radicals, C₂-C₆ polyhydroxyalkylradicals, tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals,(C₁-C₆)alkoxy(C₁-C₆)alkyl radicals, C₁-C₆ carbamylalkyl radicals,(C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals and benzyl radicals; it beingunderstood that the radical R₃ is borne by a nitrogen atom,

[0051] R₇ is chosen from C₁-C₆ alkyl radicals; C₁-C₆ monohydroxyalkylradicals; C₂-C₆ polyhydroxyalkyl radicals; aryl radicals; benzylradicals; C₁-C₆ aminoalkyl radicals; C₁-C₆ aminoalkyl radicals whereinthe amine is substituted with at least one radical chosen from(C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl, amido and (C₁-C₆)alkylsulphonylradicals; C₁-C₆ carboxyalkyl radicals; C₁-C₆ carbamylalkyl radicals;C₁-C₆ trifluoroalkyl radicals; tri(C₁-C₆)alkylsilane(C₁-C₆)alkylradicals; C₁-C₆ sulphonamidoalkyl radicals;(C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radicals;N-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylsulphonamido(C₁-C₆)alkyl radicals;

[0052] x is 0 or 1

[0053] when x=0, the linking arm D is attached to the nitrogen atom,

[0054] when x=1, the linking arm D is attached to one of the ringmembers chosen from E, G, J and L,

[0055] Y is a counter-ion.

[0056] By way of example, the ring members E, G, J and L, together withthe ring nitrogen, may form a ring chosen from pyrrole, imidazole,pyrazole, oxazole, thiazole and triazole rings. In one embodiment, thering members E, G, J and L, together with the ring nitrogen, form animidazole ring.

[0057] In another embodiment, the onium radicals Z are chosen fromradicals of formula (III), wherein x is equal to 0 and the linking arm Dis chosen from a covalent bond and an alkylene chain that may besubstituted.

[0058] The onium radicals Z may be chosen from radicals of formula (IV)

[0059] wherein:

[0060] D is a linking arm chosen from a covalent bond and linear andbranched C₁-C₁₄ alkylene chains which may be interrupted with at leastone hetero atom chosen from oxygen, sulphur and nitrogen atoms, andwhich may be substituted with at least one hydroxyl, C₁-C₆ alkoxy andamino radicals, and which may bear at least one ketone functional group;

[0061] the ring members E, G, J, L and M, which may be identical ordifferent, are each chosen from carbon, oxygen, sulphur and nitrogenatoms and, together with the ring nitrogen, form a ring chosen frompyridine, pyrimidine, pyrazine, triazine and pyridazine rings;

[0062] p is an integer ranging from 0 to 3;

[0063] m is an integer ranging from 0 to 5;

[0064] p+m is an integer ranging from 0 to 5;

[0065] R, which may be identical or different, is chosen from halogenatoms, a hydroxyl radical, C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkylradicals, C₂-C₆ polyhydroxyalkyl radicals, C₁-C₆ alkoxy radicals,tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, amido radicals, carboxylradicals, C₁-C₆ alkylcarbonyl radicals, thio radicals, C₁-C₆ thioalkylradicals, (C₁-C₆)alkylthio radicals, amino radicals, amino radicalssubstituted with at least one radical chosen from (C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl, amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆monohydroxyalkyl radicals and C₂-C₆ polyhydroxyalkyl radicals; it beingunderstood that the radical R is borne by a carbon atom,

[0066] R₃, which may be identical or different, is chosen from C₁-C₆alkyl radicals, C₁-C₆ monohydroxyalkyl radicals, C₂-C₆ polyhydroxyalkylradicals, tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals,(C₁-C₆)alkoxy(C₁-C₆)alkyl radicals, C₁-C₆ carbamylalkyl radicals,(C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals and benzyl radicals; it beingunderstood that the radical R₃ is borne by a nitrogen atom,

[0067] R₇ is chosen from C₁-C₆ alkyl radicals; C₁-C₆ monohydroxyalkylradicals; C₂-C₆ polyhydroxyalkyl radicals; aryl radicals; benzylradicals; C₁-C₆ aminoalkyl radicals; C₁-C₆ aminoalkyl radicals whereinthe amine is mono- or disubstituted with a radical or two radicals,which may be identical or different, chosen from (C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl, amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆carboxyalkyl radicals; C₁-C₆ carbamylalkyl radicals; C₁-C₆trifluoroalkyl radicals; tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals;C₁-C₆ sulphonamidoalkyl radicals; (C₁-C₆)alkylcarboxy(C₁-C₆)alkylradicals; (C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radicals;N-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylsulphonamido(C₁-C₆)alkyl radicals;

[0068] x is 0 or 1

[0069] when x=0, the linking arm D is attached to the nitrogen atom,

[0070] when x=1, the linking arm D is attached to one of the ringmembers chosen from E, G, J, L and M,

[0071] Y is a counter-ion.

[0072] In one embodiment, the ring members E, G, J, L and M form, withthe nitrogen of the ring, a ring chosen from pyridine and pyrimidinerings.

[0073] When x is equal to 0, then R is chosen, for example, from ahydroxyl radical, C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkyl radicals,C₂-C₆ polyhydroxyalkyl radicals, C₁-C₆ alkoxy radicals,tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, amido radicals, C₁-C₆alkylcarbonyl radicals, amino radicals, amino radicals mono- ordisubstituted with a radical or two radicals, which may be identical ordifferent, chosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl, amido and(C₁-C₆)alkylsulphonyl radicals; C₁-C₆ monohydroxyalkyl radicals andC₂-C₆ polyhydroxyalkyl radicals, and R₃ is chosen from C₁-C₆ alkylradicals, C₁-C₆ monohydroxyalkyl radicals, C₂-C₆ polyhydroxyalkylradicals, tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals,(C₁-C₆)alkoxy(C₁-C₆)alkyl radicals and C₁-C₆ carbamylalkyl radicals.

[0074] When x is equal to 1, R₇ is chosen, for example, from C₁-C₆ alkylradicals; C₁-C₆ monohydroxyalkyl radicals; C₂-C₆ polyhydroxyalkylradicals; C₁-C₆ aminoalkyl radicals; C₁-C₆ aminoalkyl radicals whereinthe amine is mono- or disubstituted with a radical or two radicals,which may be identical or different, chosen from (C₁-C₆)alkyl radicals,(C₁-C₆)alkylcarbonyl radicals, amido radicals and (C₁-C₆)alkylsulphonylradicals; C₁-C₆ carbamylalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals; R is chosen from a hydroxylradical, C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkyl radicals, C₂-C₆polyhydroxyalkyl radicals, C₁-C₆ alkoxy radicals,tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, amido radicals, C₁-C₆alkylcarbonyl radicals, amino radicals, amino radicals mono- ordisubstituted with a radical or two radicals, which may be identical ordifferent, chosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl, amido and(C₁-C₆)alkylsulphonyl radicals; and R₃ is chosen from C₁-C₆ alkylradicals, C₁-C₆ monohydroxyalkyl radicals, C₂-C₆ polyhydroxyalkylradicals, tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals,(C₁-C₆)alkoxy(C₁-C₆)alkyl radicals and C₁-C₆ carbamylalkyl radicals.

[0075] In one embodiment, R, R₇ and R₃ are alkyl radicals that may besubstituted.

[0076] The radical R₂ may also be chosen from onium radicals of formula—XP(O)(O—)OCH₂CH₂N⁺(CH₃)₃ wherein X is chosen from oxygen and radicals—NR₁₁, wherein R₁₁ is chosen from hydrogen, C₁-C₄ alkyl radicals andhydroxyalkyl radicals.

[0077] In one embodiment, R₂ may also be chosen from guanidine radicalsof formula —X—C═NR₈—NR₉R₁₀, wherein X is chosen from oxygen and aradical —NR₁₁, and R₈, R₉, R₁₀ and R₁₁, which may be identical ordifferent, are each chosen from hydrogen, C₁-C₄ alkyl radicals, andhydroxyalkyl radicals. In another embodiment, X is chosen from radicalsof —NR₁₁, R₈ is a hydrogen and R₉ and R₁₀, which may be identical ordifferent, are each chosen from hydrogen and alkyl radicals, forexample, a methyl radical.

[0078] The pKa of the guanidine radical R₂ is such that this substituentis present in cationic form (═NR₈H⁺) under the standard conditions forthe oxidation dyeing of hair.

[0079] As used herein, the counter-ion may be chosen from halogens suchas bromine, chlorine, fluorine and iodine, hydroxides, citrates,succinates, tartrates, lactates, tosylates, mesylates,benzenesulphonates, acetates, a hydrogen sulphate, and C₁-C₆ alkylsulphates such as methyl sulphate and ethyl sulphate.

[0080] The pyrrolidinyl-substituted para-phenylenediamine derivatives offormula (I) and the addition salts thereof may, for example, be chosenfrom: Formula Nomenclature

N′-[1-(4-Amino-phenyl)- pyrrolidin-3-yl]-N,N- dimethyl-guanidine

N-[1-(4-Amino-phenyl)- pyrrolidin-3-yl]- guanidine

3-[1-(4-Amino-phenyl)- pyrrolidin-3-yl]-1-methyl- 3H-imidazol-1-iumchloride

[1-(4-Amino-phenyl)- pyrrolidin-3-yl]-(- trimethylammonium-hexyl)-dimethyl- ammoniumdichloride

[1-(4-Amino-phenyl)- pyrrolidin-3-yl]-dimethyl- (3-trimethylsilanyl-propyl)-ammonium chloride

{2-[1-(4-Amino-phenyl)- pyrrolidin-3-yloxy]-ethyl}- trimethyl-ammoniumchloride

[1-(4-Amino-phenyl)- pyrrolidin-3-yl]- oxophosphorycholine

3-{3-[1-(4-Amino-phenyl)- pyrrolidin-3-yloxy]-propyl}-1-methyl-3H-imidazol-1- ium chloride

1-{2-[1-(4-Amino-phenyl)- pyrrolidin-3-yloxy]-ethyl}-1-methyl-pyrrolidinium chloride

3-{3-[1-(5- trimethylsilanylethyl-4- Amino-3- trimethylsilanylethyl-phenyl)-pyrrolidin-3-yloxy]- propyl}-1-methyl-3H- imidazol-1-um chloride

1-{2-[1-(4-Amino-phenyl)- pyrrolidin-3-yloxy]-ethyl}-1-methyl-piperidinium chloride

N-[1-(4-Amino-3-methyl- phenyl)-pyrrolidin-3-yl]- guanidine

N′-[1-(4-Amino-3-methyl- phenyl)-pyrrolidin-3-yl]-N,N-dimethyl-guanidine

3-[1-(4-Amino-3-methyl- phenyl)-pyrrolidin-3-yl]-1-methyl-3H-imidazol-1-ium chloride

[1-(4-Amino-3-methyl- phenyl)-pyrrolidin-3-yl]- dimethyl-(3-trimethylsilanyl-propyl ammonium chloride

[1-(4-Amino-3-methyl- phenyl)-pyrrolidin-3-yl]-(-trimethylammonium-hexyl)- dimethyl-ammonium dichloride

[1-(4-Amino-3-methyl- phenyl)-pyrrolidin-3-yl]- oxophosphorycholine

{8-[1-(4-Amino-3-methyl- phenyl)-pyrrolidin-3-yloxy]-ethyl}-trimethyl-ammonium chloride

1-{2-[1-(4-Amino-3- methyl-phenyl)-pyrrolidin- 3-yloxy]-ethyl}-1-methyl-pyrrolidinium chloride

3-{3-[1-(4-Amino-3-methyl- phenyl)-pyrrolidin-3-yloxy]-propyl}-1-methyl-3H- imidazol-1-um chloride

1-{2-[1-(4-Amino-3- methyl-phenyl)-pyrrolidin- 3-yloxy]-ethyl}-1-methyl-piperidine

3-[1-(5- trimethylsilanylethyl-4- Amino-3- trimethylsilanylethyl-phenyl)-pyrrolidin-3-yl]-1- methyl-3H-imidazol-1-ium chloride

3-[1-(4-Amino-3- trimethylsilanylethyl- phenyl)-pyrrolidin-3-yl]-1-methyl-3H-imidazol-1-ium chloride

3-{3-[1-(4-Amino-3- trimethylsilanylethyl- phenyl)-pyrrolidin-3-yloxy]-propyl}-1-methyl-3H- imidazol-1-ium chloride

1′(4-Amino-phenyl)-1- methyl-[1,3′]bipyrrolidinyl- 1-ium chloride

1′-(4-Amino-3-methyl- phenyl)-1-methyl- [1,3′]bipyrrolidinyl-1-iumchloride

3-{[1-(4-Amino-phenyl)- pyrrolidin-3-ylcarbamoyl]- methyl}-1-methyl-3H-imidazol-1-ium chloride

3-{[1-(4-Amino-3-methyl- phenyl)-pyrrolidin-3- ylcarbamoyl]-methyl}-1-methyl-3H-imidazol-1-ium chloride

3-[1-(4-Amino-phenyl)- pyrroldin-3-yl]-1-(3- trimethylsilanyl-propyl)-3H-imidazol-1- iumchloride

3-[1-(4-Amino-3-methyl- phenyl)-pyrrolidin-3-yl]-1-(3-trimethylsilanyl-propyl)- 3H-imidazol-1-ium chloride

3-[1-(4-Amino-phenyl)- pyrrolidin-3-yl]-thiazol-3- ium Acetate

1-[1-(4- aminophenyl)pyrrolidin-3- yl]pyridinium Acetate

1-[1-(4-Amino-phenyl)- pyrrolidin-3-yl]-4-aza-1-azonia-bicyclo[2,2,2]octane; methanesulfonate hydrochloride

[0081] The pyrrolidinyl-substituted para-phenylenediamine derivatives offormula (I) and addition salts thereof may, for example, be chosen from:

[0082] N′-[1-(4-Aminophenyl)pyrrolidin-3-yl]-N,N-dimethylguanidine;

[0083] N-[1-(4-Aminophenyl)pyrrolidin-3-yl]guanidine;

[0084] 3-[1-(4-Aminophenyl)pyrrolidin-3-yl]-1-methyl-3H-imidazol-1-iumchloride;

[0085][1-(4-Aminophenyl)pyrrolidin-3-yl]dimethyl-(3-trimethylsilanylpropyl)ammoniumchloride;

[0086]N′-[1-(4-Amino-3-methylphenyl)pyrrolidin-3-yl]-N,N-dimethylguanidine;

[0087] N-[1-(4-Amino-3-methylphenyl)pyrrolidin-3-yl]guanidine;

[0088]3-[1-(4-Amino-3-methylphenyl)pyrrolidin-3-yl]-1-methyl-3H-imidazol-1-iumchloride;

[0089][1-(4-Amino-3-methylphenyl)pyrrolidin-3-yl]dimethyl-(3-trimethylsilanylpropylammoniumchloride;

[0090]3-[1-(4-Aminophenyl)pyrrolidin-3-yl]-1-(3-trimethylsilanylpropyl)-3H-imidazol-1-iumchloride;

[0091]3-[1-(4-Amino-3-methylphenyl)pyrrolidin-3-yl]-1-(3-trimethylsilanylpropyl)-3H-imidazol-1-iumchloride;

[0092] 1′-(4-Aminophenyl)-1-methyl-[1,3′]bipyrrolidinyl-1-ium chloride;

[0093] 1′-(4-Amino-3-methylphenyl)-1-methyl-[1,3′]bipyrrolidinyl-1-iumchloride;

[0094]3-{[1-(4-Aminophenyl)pyrrolidin-3-ylcarbamoyl]methyl}-1-methyl-3H-imidazol-1-iumchloride;

[0095]3-{[1-(4-Amino-3-methylphenyl)pyrrolidin-3-ylcarbamoyl]methyl}-1-methyl-3H-imidazol-1-iumchloride; and

[0096] 1′-(4-amino-phenyl)-1-methyl-[1,3′]bipyrrolidinyl-1-ium chloride.

[0097] According to one embodiment, the linking arm D comprises at leastone phosphoryl radical, for example, at least one radical chosen from[1-(4-Amino-phenyl)-pyrrolidin-3-yl]-oxophosphorylcholine and[1-(4-Amino-3-methyl-phenyl)-pyrrolidin-3-yl]-oxophosphorylcholine.

[0098] The dye composition disclosed herein comprises, in a mediumsuitable for dyeing keratin fibers, such as human hair, at least oneoxidation base chosen from pyrrolidinyl-substitutedpara-phenylenediamine derivatives of formula (I) and the addition saltsthereof as defined above.

[0099] The at least one oxidation base may be present in an amountranging, for example, from 0.001% to 10% by weight, relative to thetotal weight of the dye composition, further for example, from 0.005% to6% by weight, relative to the total weight of the dyeing composition.

[0100] The dye composition disclosed herein may further comprise atleast one coupler conventionally used for dyeing keratin fibers. The atleast one coupler may, for example, be chosen frommeta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthaleniccouplers and heterocyclic couplers, and the addition salts thereof.

[0101] The at least one coupler may, for example, be chosen from2-methyl-5-aminophenol, 5-N-(P-hydroxyethyl)amino-2-methylphenol,6-chloro-2-methyl-5-aminophenol, 3-aminophenol, 1,3-dihydroxybenzene,1,3-dihydroxy-2-methylbenzene, 4-chloro-1,3-dihydroxybenzene,2,4-diamino-1-(β-hydroxyethyloxy)benzene,2-amino-4-(β-hydroxyethylamino)-1-methoxybenzene, 1,3-diaminobenzene,1,3-bis(2,4-diaminophenoxy)propane, 3-ureidoaniline,3-ureido-1-dimethylaminobenzene, sesamol,1-β-hydroxyethylamino-3,4-methylenedioxybenzene, α-naphthol,2-methyl-1-naphthol, 6-hydroxyindole, 4-hydroxyindole,4-hydroxy-N-methylindole, 2-amino-3-hydroxypyridine,6-hydroxybenzomorpholine, 3,5-diamino-2,6-dimethoxypyridine,1-N-(β-hydroxyethyl)amino-3,4-methylenedioxybenzene and2,6-bis(β-hydroxyethylamino)toluene and the acid addition salts thereof.

[0102] In one embodiment, the at least one coupler is present in anamount ranging from 0.001% to 10% by weight, relative to the totalweight of the dye composition, further for example, from 0.005% to 6% byweight, relative to the total weight of the dye composition.

[0103] In another embodiment, the dye composition may also comprise atleast one additional oxidation base conventionally used in oxidationdyeing, other than those described above. The at least one additionaloxidation base may, for example, be chosen from para-phenylenediaminesother than those described above, such as bis(phenyl)alkylenediamines,para-aminophenols, bis-para-aminophenols, ortho-aminophenols andheterocyclic bases, and the addition salts thereof.

[0104] The para-phenylenediamines may, for example, be chosen frompara-phenylenediamine, para-tolylenediamine,2-chloro-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine,2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-para-phenylenediamine,2,5-dimethyl-para-phenylenediamine, N,N-dimethyl-para-phenylenediamine,N,N-diethyl-para-phenylenediamine, N,N-dipropyl-para-phenylenediamine,4-amino-N,N-diethyl-3-methylaniline,N,N-bis(P-hydroxyethyl)-para-phenylenediamine,4-N,N-bis(β-hydroxyethyl)amino-2-methylaniline,4-N,N-bis(β-hydroxyethyl)amino-2-chloroaniline,2-β-hydroxyethyl-para-phenylenediamine, 2-fluoro-para-phenylenediamine,2-isopropyl-para-phenylenediamine,N-(β-hydroxypropyl)-para-phenylenediamine,2-hydroxymethyl-para-phenylenediamine,N,N-dimethyl-3-methyl-para-phenylenediamine, N-ethyl-N-(P-hydroxyethyl)-para-phenylenediamine,N-(β,β-dihydroxypropyl)-para-phenylenediamine,N-(4′-aminophenyl)-para-phenylenediamine,N-phenyl-para-phenylenediamine,2-β-hydroxyethyloxy-para-phenylenediamine,2-β-acetylaminoethyloxy-para-phenylenediamine,N-(β-methoxyethyl)-para-phenylenediamine, 4-aminophenylpyrrolidine,2-thienyl-para-phenylenediamine, 2-β-hydroxyethylamino-5-aminotolueneand 3-hydroxy-1-(4′-aminophenyl)pyrrolidine, and the acid addition saltsthereof.

[0105] The para-phenylenediamines may, for example, be chosen frompara-phenylenediamine, para-tolylenediamine,2-isopropyl-para-phenylenediamine,2-β-hydroxyethyl-para-phenylenediamine,2-β-hydroxyethyloxy-para-phenylenediamine,2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-para-phenylenediamine,2,3-dimethyl-para-phenylenediamine,N,N-bis(β-hydroxyethyl)-para-phenylenediamine,2-chloro-para-phenylenediamine and2-β-acetylaminoethyloxy-para-phenylenediamine, and the acid additionsalts thereof.

[0106] The bis(phenyl)alkylenediamines may be chosen, for example, fromN,N′-bis(β-hydroxyethyl)-N,N′-bis(4′-aminophenyl)-1,3-diaminopropanol,N,N′-bis(β-hydroxyethyl)-N,N′-bis(4′-aminophenyl)ethylenediamine,N,N′-bis(4-aminophenyl)tetra-methylenediamine, N,N′-bis(p-hydroxyethyl)-N,N′-bis(4-aminophenyl)tetramethylenediamine,N,N′-bis(4-methyl-aminophenyl)tetramethylenediamine,N,N′-bis(ethyl)-N,N′-bis(4′-amino-3′-methylphenyl)ethylenediamine and1,8-bis(2,5-diaminophenoxy)-3,6-dioxaoctane, and the acid addition saltsthereof.

[0107] The para-aminophenols may be chosen, for example, frompara-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol,4-amino-3-hydroxymethylphenol, 4-amino-2-methylphenol,4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol,4-amino-2-aminomethylphenol, 4-amino-2-(β-hydroxyethylaminomethyl)phenoland 4-amino-2-fluorophenol, and the acid addition salts thereof.

[0108] The ortho-aminophenols may be chosen, for example, from2-aminophenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol and5-acetamido-2-aminophenol, and the acid addition salts thereof.

[0109] The heterocyclic bases, may be chosen, for example, from pyridinederivatives, pyrimidine derivatives and pyrazole derivatives.

[0110] The pyridine derivatives may be chosen from compounds disclosed,for example, in Patent Nos. GB 1 026 978 and GB 1 153 196, such as2,5-diaminopyridine, 2-(4-methoxyphenyl)amino-3-aminopyridine,2,3-diamino-6-methoxypyridine,2-(β-methoxyethyl)amino-3-amino-6-methoxypyridine and3,4-diaminopyridine, and the acid addition salts thereof.

[0111] The pyridine oxidation bases may also be chosen, for example,from 3-aminopyrazolo[1,5-a]pyridine oxidation bases and the additionsalts thereof disclosed, for example, in Patent Application No. FR 2 801308. For example, the pyridine oxidation bases may be chosen frompyrazolo[1,5-a]pyrid-3-ylamine;2-acetylaminopyrazolo[1,5-a]pyrid-3-ylamine;2-morpholin-4-ylpyrazolo[1,5-a]pyrid-3-ylamine;3-aminopyrazolo[1,5-a]pyridine-2-carboxylic acid,2-methoxypyrazolo[1,5-a]pyrid-3-ylamine;(3-aminopyrazolo[1,5-a]pyrid-7-yl)methanol;2-(3-aminopyrazolo[1,5-a]pyrid-5-yl)ethanol;2,3-aminopyrazolo[1,5-a]pyrid-7-yl)ethanol;(3-aminopyrazolo[1,5-a]pyrid-2-yl)methanol;3,6-diaminopyrazolo[1,5-a]pyridine; 3,4-diaminopyrazolo[1,5-a]pyridine;pyrazolo[1,5-a]pyridine-3,7-diamine;7-morpholin-4-ylpyrazolo[1,5-a]pyrid-3-ylamine;pyrazolo[1,5-a]pyridine-3,5-diamine;5-morpholin-4-ylpyrazolo[1,5-a]pyrid-3-ylamine;2-[(3-aminopyrazolo[1,5-a]pyrid-5-yl)(2-hydroxyethyl)amino]ethanol;2-[(3-aminopyrazolo[1,5-a]pyrid-7-yl)(2-hydroxyethyl)amino]ethanol;3-aminopyrazolo-[1,5-a]pyrid-5-ol; 3-aminopyrazolo[1,5-a]pyrid-4-ol;3-aminopyrazolo[1,5-a]pyrid-6-ol; 3-aminopyrazolo[1,5-a]pyrid-7-ol andthe acid and base addition salts thereof.

[0112] The pyrimidine derivatives may be chosen, for example, from thecompounds disclosed in Patent Nos. DE 2 359 399 and JP 88-169 571; JP 0563 124; EP 0 770 375 and Patent Application No. WO 96/15765, such as2,4,5,6-tetraaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine,2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidineand 2,5,6-triaminopyrimidine, and pyrazolopyrimidine derivatives such asthose disclosed in Patent Application FR-A-2 750 048 such aspyrazolo[1,5-a]pyrimidine-3,7-diamine;2,5-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine;pyrazolo[1,5-a]pyrimidine-3,5-diamine;2,7-dimethylpyrazolo[1,5-a]pyrimidine-3,5-diamine;3-aminopyrazolo[1,5-a]pyrimidin-7-ol;3-aminopyrazolo[1,5-a]pyrimidin-5-ol;2-(3-aminopyrazolo[1,5-a]pyrimidin-7-ylamino)ethanol,2-(7-aminopyrazolo[1,5-a]pyrimidin-3-ylamino)ethanol,2-[(3-aminopyrazolo[1,5-a]pyrimidin-7-yl)(2-hydroxyethyl)amino]ethanol,2-[(7-aminopyrazolo[1,5-a]pyrimidin-3-yl)(2-hydroxyethyl)amino]ethanol,5,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine,2,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine,2,5,N7,N7-tetramethylpyrazolo[1,5-a]pyrimidine-3,7-diamine and3-amino-5-methyl-7-imidazolylpropylaminopyrazolo[1,5-a]pyrimidine, andthe acid addition salts thereof and the tautomeric forms thereof, when atautomeric equilibrium exists.

[0113] The pyrazole derivatives may be chosen from compounds disclosedin Patent Nos. DE 3 843 892 and DE 4 133 957 and Patent Application Nos.WO 94/08969, WO 94/08970, FR-A-2 733 749 and DE 195 43 988, such as4,5-diamino-1-methylpyrazole, 4,5-diamino-1-(β-hydroxyethyl)pyrazole,3,4-diaminopyrazole, 4,5-diamino-1-(4′-chlorobenzyl)pyrazole,4,5-diamino-1,3-dimethylpyrazole, 4,5-diamino-3-methyl-1-phenylpyrazole,4,5-diamino-1-methyl-3-phenylpyrazole,4-amino-1,3-dimethyl-5-hydrazinopyrazole,1-benzyl-4,5-diamino-3-methylpyrazole,4,5-diamino-3-tert-butyl-1-methylpyrazole,4,5-diamino-1-tert-butyl-3-methylpyrazole,4,5-diamino-1-(β-hydroxyethyl)-3-methylpyrazole,4,5-diamino-1-ethyl-3-methylpyrazole,4,5-diamino-1-ethyl-3-(4′-methoxyphenyl)pyrazole,4,5-diamino-1-ethyl-3-hydroxymethylpyrazole,4,5-diamino-3-hydroxymethyl-1-methylpyrazole,4,5-diamino-3-hydroxymethyl-1-isopropylpyrazole,4,5-diamino-3-methyl-1-isopropylpyrazole,4-amino-5-(2′-aminoethyl)amino-1,3-dimethylpyrazole,3,4,5-triaminopyrazole, 1-methyl-3,4,5-triaminopyrazole,3,5-diamino-1-methyl-4-methylaminopyrazole and3,5-diamino-4-(β-hydroxyethyl)amino-1-methylpyrazole, and the acidaddition salts thereof.

[0114] The at least one additional oxidation base may be present in thedye composition in an amount ranging, for example, from 0.001% to 10% byweight, relative to the total weight of the dye composition, further forexample, from 0.005% to 6% by weight, relative to the total weight ofthe composition.

[0115] The addition salts of the at least one oxidation base, of the atleast one additional oxidation base, and of the at least one coupler maybe chosen, for example, from the acid addition salts, such as thehydrochlorides, hydrobromides, sulphates, citrates, succinates,tartrates, lactates, tosylates, benzenesulphonates, phosphates andacetates, and the base addition salts, such as sodium hydroxide,potassium hydroxide, ammonia, amines and alkanolamines.

[0116] In another embodiment, the dye composition disclosed herein mayalso comprise at least one direct dye chosen, for example, fromnitrobenzene dyes, azo direct dyes and methine direct dyes. The at leastone direct dye may be of nonionic, anionic or cationic nature.

[0117] The medium suitable for dyeing, also known as the dye support,comprises water or a mixture of water and at least one organic solventto dissolve the compounds that are not sufficiently soluble in water.The at least one organic solvent may, for example, be chosen from C₁-C₄lower alkanols, such as ethanol and isopropanol; polyols and polyolethers such as 2-butoxyethanol, propylene glycol, propylene glycolmonomethyl ether, diethylene glycol monoethyl ether and monomethylether, as well as aromatic alcohols such as benzyl alcohol andphenoxyethanol.

[0118] The at least one organic solvent may be present in an amountranging, for example, from 1% to 40% by weight, relative to the totalweight of the dye composition, further for example, from 5% to 30% byweight, relative to the total weight of the dyeing composition.

[0119] In another embodiment, the dye composition may also comprise, forexample, at least one adjuvant conventionally used in compositions fordyeing the hair. For example, the at least one adjuvant may be chosenfrom anionic, cationic, nonionic, amphoteric and zwitterionicsurfactants, anionic, cationic, nonionic, amphoteric and zwitterionicpolymers, inorganic and organic thickeners, for example, anionic,cationic, nonionic and amphoteric associative polymeric thickeners,antioxidants, penetration agents, sequestering agents, fragrances,buffers, dispersing agents, packaging agents, for example, volatile andnon-volatile, modified and unmodified silicones, film-forming agents,ceramides, preserving agents and opacifiers.

[0120] The at least one adjuvant may be present in an amount ranging,for example, from 0.01% to 20% by weight, relative to the weight of thecomposition.

[0121] A person skilled in the art may choose at least one optionaladditional compound such that the advantageous properties intrinsicallyassociated with the oxidation dye composition disclosed herein are not,or are not substantially, adversely affected by the addition envisaged.

[0122] The pH of the dye composition disclosed herein may range, forexample, from 3 to 12, further for example, from 5 to 11. The pH may beadjusted to the desired value using, for example, at least one agentchosen from acidifying and basifying agents. The acidifying agents andthe basifying agents may be chosen, for example, from thoseconventionally used in the dyeing of keratin fibers and standard buffersystems.

[0123] The acidifying agents may, for example, be chosen from inorganicand organic acids such as hydrochloric acid, orthophosphoric acid,sulphuric acid, carboxylic acids such as acetic acid, tartaric acid,citric acid and lactic acid, and sulphonic acids.

[0124] The basifying agents may, for example, be chosen from aqueousammonia, alkaline carbonates, alkanolamines such as mono-, di- andtriethanolamine and derivatives thereof, sodium hydroxide, potassiumhydroxide and the compounds of formula (V) below:

[0125] wherein W is chosen from propylene residues optionallysubstituted with at least one radical chosen from a hydroxyl radical andC₁-C₄ alkyl radicals; R_(a), R_(b), R_(c) and R_(d), which may beidentical or different, are each chosen from hydrogen, C₁-C₄ alkylradicals and C₁-C₄ hydroxyalkyl radicals.

[0126] The dye composition disclosed herein may be in various forms,such as in a form chosen from liquids, creams, gels, and any other formthat may be suitable for dyeing keratin fibers, such as human hair.

[0127] Further disclosed herein is a process comprising applying the dyecomposition disclosed herein to keratin fibers, wherein the color may bedeveloped using at least one oxidizing agent. The color may bedeveloped, for example, at acidic, neutral or alkaline pH. The at leastone oxidizing agent may be added to the dye composition disclosed hereinat the time of use, or an oxidizing composition comprising at least oneoxidizing agent may, be applied simultaneously or sequentially to thedye composition disclosed herein.

[0128] In one embodiment, the dye composition disclosed herein may bemixed, for example, at the time of use, with an oxidizing compositioncomprising, in a medium suitable for dyeing, at least one oxidizingagent. The at least one oxidizing agent is present in an amount that issufficient to develop a coloration. The mixture obtained then may beapplied to the keratin fibers. After an action time ranging from 3 to 50minutes, for example, from 5 to 30 minutes, the keratin fibers may berinsed, washed with shampoo, rinsed again and then dried.

[0129] The at least one oxidizing agent used for the oxidation dyeing ofkeratin fibers may be chosen, for example, from hydrogen peroxide, ureaperoxide, alkali metal bromates, persalts such as perborates andpersulphates, peracids and oxidase enzymes, such as peroxidases,2-electron oxidoreductases such as uricases, and 4-electron oxygenases,such as laccases. In one embodiment, the at least one oxidizing agent ishydrogen peroxide.

[0130] The oxidizing composition may also comprise at least one adjuvantchosen from those conventionally used in compositions for dyeing thehair, such as those adjuvants defined above.

[0131] The pH of the oxidizing composition comprising the at least oneoxidizing agent may be such that, after mixing with the dye composition,the pH of the resulting composition applied to the keratin fibersranges, for example, from 3 to 12, further for example, from 5 to 11.The pH may be adjusted to the desired value using, for example, at leastone agent chosen from acidifying and basifying agents. The acidifyingand basifying agents may be chosen from those conventionally used in thedyeing of keratin fibers and standard buffer systems as defined above.

[0132] The ready-to-use composition that is finally applied to thekeratin fibers may, for example, be in various forms, such as in a formchosen from liquids, creams and gels and any other form that is suitablefor dyeing keratin fibers, such as human hair.

[0133] Further disclosed herein is a multi-compartment dyeing device or“kit”, comprising a first compartment comprising the dye compositiondisclosed herein and a second compartment comprising the oxidizingcomposition. This device may, for example, be equipped with a means forapplying the desired mixture to the hair, such as the devices disclosedin Patent No. FR-2 586 913.

[0134] Using this device, it is possible to dye keratin fibers using aprocess comprising mixing a dye composition comprising at least oneoxidation base chosen from pyrrolidinyl-substitutedpara-phenylenediamine derivative of formula (I) and the addition saltsthereof with at least one oxidizing agent, and applying the mixtureobtained to the keratin fibers for a time that is sufficient to developthe desired coloration.

[0135] Even further disclosed herein are nitro pyrrolidinyl-substitutedpara-phenylenediamine derivatives of formula (I′) and the addition saltsthereof, such derivatives being intermediate compounds in the synthesisof pyrrolidinyl-substituted para-phenylenediamine derivatives of formula(I).

[0136] wherein R₁, n and R₂ are previously defined herein.

[0137] The pyrrolidinyl-substituted para-phenylenediamine derivatives offormula (I) and the addition salts thereof as disclosed herein can beprepared by the application or adaptation of known methods. For example,they can be obtained by the adaptation of the methods disclosed below.

[0138] The examples that follow serve to illustrate the inventionwithout, however, being limiting in nature.

EXAMPLES Example 1 Synthesis of1-methyl-3-[1-(4-aminophenyl)pyrrolidin-3-yl]-3H-imidazol-1-ium chloridehydrochloride

[0139]

Synthesis of 1-(4-nitrophenyl)pyrrolidin-3-ol (1)

[0140] 2 g of 1-fluoro-4-nitrobenzene (0.0155 mol), 1.3 g of sodiumhydrogen carbonate (0.0155 mol) and 15 ml of a dioxane/water mixture(8/2) were placed in a three-necked flask. 1.35 g of 3-pyrrolidinol(0.0155 mol) was rapidly added to this mixture. The heterogeneousmixture was heated at reflux (87° C.) for 10 hours. The reaction mixturewas then poured into ice-water; a yellow precipitate was obtained, whichwas filtered off and rinsed with water. After drying under vacuum in thepresence of P₂O₅, 2.95 g of a yellow solid are obtained (97% yield).

[0141]¹H NMR (DMSO-d₆, 200 MHz, ppm) in accordance with the expectedproduct: 8.04 (d, J=9 Hz, 2H); 6.58 (d, J=9 Hz, 2H); 5.06 (d, J=3.6 Hz,1H); 4.41 (m, 1H); 3.45 (m, 3H); 3.20 (m, 1H); 2.04 (m, 2H). Elementalanalysis: % C H N O Calculated 57.89 5.81 13.45 23.05 Found 57.17 5.7213.23 23.28

Synthesis of 1-(4-aminophenyl)pyrrolidin-3-yl methanesulphonate (2)

[0142] 40 ml (0.516 mol) of mesyl chloride was added dropwise at 5° C.to 83.3 g (0.4 mol) of N-(4-nitrophenyl)-3-hydroxypyrrolidine (1)dissolved in 625 ml of anhydrous THF and 72.7 ml (0.6 mol) oftriethylamine. The mixture was allowed to return to room temperature andwas then poured onto ice. After filtering off the precipitate by suctionand drying, 109 g of yellow powder (2) was obtained.

[0143] Melting point: 203° C.

[0144]¹H NMR (400 MHz-DMSO) ppm 8.09 (d, 2H); 6.68 (d, 2H); 5.47 (m,1H);3.77-3.48 (m, 4H); 3.28 (s, 3H); 2.35 (m, 2H).

[0145] ESI+MASS: m/z=287 [MH+].

Synthesis of 1-methyl-3-[1-(4-nitrophenyl)pyrrolidin-3-yl]-3H-imidazol-1-iummethanesulphonate (3)

[0146] 23 g (0.08 mol) of 1-(4-nitrophenyl)pyrrolidin-3-ylmethanesulphonate (2) was heated for 8 hours at 85° C. in 150 g of1-methylimidazole (1.82 mol). This solution was stirred in 2 l of ethylacetate to the point of crystallization. After filtration and drying, 24g of yellow powder (3) was obtained.

[0147]¹H NMR (400 MHz-DMSO) ppm 9.44 (s, 1H); 8.29 (d, 2H); 8.07 (m,1H);7.96 (m,1H); 6.91 (d, 2H); 5.48 (m, 1H); 4.16 (m, 1H); 4.02 (s, 3H) from3.98 to 3.79 (m, 4H); 2.85 (m, 1H); 2.69 (m, 1H); 2.50 (s, 3H).

[0148] ESI+mass: m/z=273 [M+].

Synthesis of1-methyl-3-[1-(4-nitrophenyl)pyrrolidin-3-yl]-3H-imidazol-1-ium chloride(4)

[0149] 23 g (0.0624 mol) of1-methyl-3-[1-(4-nitrophenyl)pyrrolidin-3-yl]-3H-imidazol-1-iummethanesulphonate (3) dissolved in 200 ml of water was stirred with 500g of Amberlite IRA-402 ion-exchange resins for 14 hours; the resin wasseparated out by filtration and the filtrate was concentrated and thentaken up in isopropanol. The yellow powder was recovered by filtrationand then dried. 16.5 g of1-methyl-3-[1-(4-nitrophenyl)pyrrolidin-3-yl]-3H-imidazol-1-ium chloride(4) was obtained.

[0150]¹H NMR (400 MHz-DMSO) ppm 9.35 (s, 1H); 8.11 (m, 2H); 8.90 (m,1H); 7.78 (m, 1H); 6.71 (m, 2H); 5.31 (m, 1H); 4.37 (m, 1H); from 3.98to 3.95 (m, 1H); 3.85 (s, 3H); from 3.83 to 3.69 (m, 4H); from 2.51 to2.49 (m, 2H);

[0151] ESI+mass: m/z=307 [M+].

Synthesis of1-methyl-3-[1-(4-aminophenyl)pyrrolidin-3-yl]-1H-imidazol-1-ium chloridehydrochloride (5)

[0152] 16 g (0.0518 mol) of the preceding derivative (4) dissolved in600 ml of ethanol was hydrogenated in the presence ofpalladium-on-charcoal under a hydrogen pressure of 8 bar. Afterfiltering off the catalyst, the expected derivative (5) was isolated inthe form of the hydrochloride.

[0153]¹H NMR (400 MHz-DMSO) ppm 8.86 (s 1H); 7.59 (t, 1H); 7.54 (t, 1H);7.41 (m, 2H); 6.89 (m, 2H); 5.33 (m, 1H); 3.97 (m, 3H); 3.85 (m, 2H);3.71 (m, 1H); 3.50 (m, 1H); 2.76 (m,1H); 2.51 (m, 1H);

[0154] ESI+mass: m/z=243 [M+].

Example 2 Synthesis of1′-(4-Amino-phenyl)-1-methyl-1,3′]bipyrrolidinyl-1-ium chloridehydrochloride

[0155]

Synthesis of 1′-(4-Nitro-phenyl)-[1,3′]bipyrrolidinyl (1)

[0156] 5 g (0.0174 mole) of methanesulfonic acid1-(4-nitro-phenyl)-pyrrolidin-3yl ester (2) were heated 2 hours at 85°C. in 30 ml of pyrrolidine. The mixture was then poured on ice wateruntil crystallization occurred. After filtrating and drying, theobtained yellow powder was chromatographed with an eluent consisting ofdichloromethane/methanol (98/2). 2.6 g of derivative (1) was thusobtained (yield 53%).

[0157] melting point=114° C.

[0158] RMN 1H (400MHz, DMSO) ppm 8.04(m, 2H); 6.61(m, 2H); 3.60(m, 2H);3.40(m, 1H); 3.24(m, 1H); 2.86(m,1H); 2.50(m, 2H); 2.16(m, 1H); 1.92(m,1H); 1.70(m, 4H).

[0159] ESI+Mass: m/z=262(MH+)

Synthesis of 1-Methyl-1′-(4-nitro-phenyl)-[1,3′]bipyrrolidinyl-1-ium;chloride (3)

[0160] 24.8 g (0.095 mole) of 1′-(4-Nitro-phenyl)-[1,3′]bipyrrolidinyl(1) were mixed with 330 ml of ethylacetate. 10 ml (0.105 mole) ofdimethylsulfate were added and the mixture was heated at reflux for 4hours. At ambient temperature, the yellow powder thus obtained wasfiltered off, washed with ethyl acetate and dried under vacuum. The ionswere exchanged on Amberlite IRA-402 resin. 21 g of a yellow powder wereobtained (3) (yield 75%).

[0161] RMN 1H (400 MHz, D2O) ppm 7.96(m, 2H); 6.51(m, 2H); 4.3(m, 1H);3.78-3.39(m, 8H); 2.98(s,3H); 2.97-2.42(m, 2H);2.16(m, 4H)

[0162] ESI+Mass: m/z=276(M+)

Synthesis of 1′-(4-Amino-phenyl)-1-methyl-[1,3′]bipyrrolidinyl-1-iumchloride, hydrochloride

[0163] 21 g (0.067 mole) of the preceding derivative (3) in 700 ml ofethanol was hydrogenated in presence of palladium on charcoal underhydrogen pressure of 10 bars; after filtration of the catalyst, thederivative (4) was isolated under hydrochloride form.

[0164] RMN 1H (400 MHz, DMSO) ppm 2,29 (m, 4H); 2,49 (m,1H); 2,63 (m,1H); 3,1 (s, 3H); 3,35 (m, 1H); 3,69 (m, 7H); 3,8 (dd, 1H); 4,42 (m,1H); 6,86 (m, 2H); 7,35 (m, 2H)

[0165] ESI+Mass: m/z=246(M+)

Example 3 Synthesis of3-[1-(4-Amino-3-methyl-phenyl)-pyrrolidin-3-yl]-1-methyl-3Himidazol-1-iumchloride hydrochloride

[0166]

Synthesis of 1-(3-Methyl-4-nitro-phenyl)-pyrrolidin-3-ol (1)

[0167] In a three necked flask, 38.78 g of 5-fluoro-2-nitrotoluene (0.25mol), 41.4 g of potassium carbonate (0.3 mol) and 200 ml ofN-methylpyrrolidinone were mixed. 26.13 g of 3-pyrrolidinol (0.3 mol)were added to this mixture. The heterogeneous mixture was agitated atambient temperature for 12 hours. The reacting mixture was then pouredon ice water. A yellow powder was then obtained. The powder was thenfiltered off and rinsed with water. After drying under vacuum with P₂O₅,55.56 g of a yellow solid were obtained (yield) (95%).

[0168] RMN 1H (400 MHz-DMSO) ppm 8.01 (d, 1H); 6.50-6.46 (m, 2H);5.04(m,1H); 4.42 (m, 1H) 3.50-3.42 (m, 3H); 3.24-3.21 (m, 1H); 2.56 (s,3H); 2.15-1.90 (m, 2H).

Synthesis of 1-(3-methyl-4-nitro-phenyl)-pyrrolidin-3-yl methanesulfonic ester (2)

[0169] 35.56 g (0.16 mole) of1-(3-Methyl-4-nitro-phenyl)-pyrrolidin-3-ol (1) in 500 ml of anhydrousTHF and 29 ml (0.24 mole) of triethylamine were mixed drop to drop with16 ml (0.21 mole) of mesyl chloride at 5° C. At ambient temperature, themixture was agitated for 1 hour then poured on ice water. Afterfiltering and drying, 48 g of a yellow powder were obtained (2).

[0170] RMN 1H (400 MHz-DMSO) ppm 7.98-7.95 (m, 1H); 6.50-6.47 (m, 2H);5.4 (m, 1H); 3.64-3.39 (m, 4H); 3.21 (s, 3H); 2.50 (s, 3H); 2.27-2.24(m, 2H).

Synthesis of1-Methyl-3-[1-(3-methyl-4-nitro-phenyl)-pyrrolidin-3-yl]-3H-imidazol-1-iummethanesulfonate (3)

[0171] 6 g (0.02 mole) of 1-(3-methyl-4-nitro-phenyl)-pyrrolidin-3-ylmethane sulfonic ester (2) were heated 12 hours at 90° C. in 30 ml of1-methylimidazole. The solution was agitated in 2 l of ethylacetateuntil crystallization. After filtering off and drying, 6.6 g of a yellowpowder were obtained (3).

[0172] RMN 1H (400 MHz-DMSO) ppm 8.07 (s, 1H); 7.72 (m, 1H); 7.43 (s,1H); 7.42 (m, 1H); 6.28-6.23 (m, 2H); 5.16 (m, 1H); 3.81-3.77 (m, 4H);3.67-3.43 (m, 3H); 2.68 (s, 3H); 2.59 (m, 1H); 2.35 (m,1H); 2.28 (s,3H).

[0173] ESI+Mass: m/z=287[M+]

Synthesis of1-Methyl-3-[1-(3-methyl-4-nitro-phenyl)-pyrrolidin-3-yl]-3H-imidazol-1-iumchloride

[0174] 6.5 g (0.017 mole) of1-Methyl-3-[1-(3-methyl-4-nitro-phenyl)-pyrrolidin-3-yl]-3H-imidazol-1-iummethanesulfonate (3) in 200 ml of water were agitated with 200 g of anion-exchange resin Amberlite IRA-402 for 12 hours. The resin wasseparated by filtration, the filtrate was concentrated then mixed withisopropanol. A yellow powder was then obtained after filtering off anddrying (3.4 g).

[0175] RMN 1H (400 MHz-DMSO) ppm 8.72 (s, 1H); 7.65 (m, 1H); 7.43 (s,1H); 7.37 (m, 1H); 6.22-6.17 (m, 2H); 5.16 (m, 1H); 3.78 (m, 4H);3.64-3.40 (m, 3H); 2.60-2.56 (m, 1H); 2.40-2.37 (m, 1H) 2.23 (s, 3H).

[0176] ESI+Mass: m/z=287[M+]

Synthesis of1-methyl-3-[1-(3-methyl-4-amino-phenyl)-pyrrolidin-3-yl]-3H-imidazol-1-iumchloride, hydrochloride (5)

[0177] 3.2 g (0.01 mole) of derivative (4) in 300 ml of ethanol werehydrogenated in the presence of palladium on charcoal under hydrogenpressure of 9 bars. The catalyst was removed by filtration. Thederivative (5) was isolated under chloride form.

[0178] RMN 1H (400 MHz-DMSO) ppm 7,35 (m, 2H); 6,86 (m, 2H); 4,42 (m,1H); 3,8 (dd, 1H); 3,69 (m, 7H); 3,35 (m,1H); 3,1 (s, 3H); 2,63 (m,1H);2,49 (m, 1H); 2,29 (m, 4H).

[0179] ESI+Mass: m/z=257[M+]

Example 4 Synthesis of N-[10(4-aminophenyl)pyrrolidin-3-yl]guanidinetrihydrochloride

[0180]

Synthesis of N-[1-(4-nitrophenyl)pyrrolidin-3-yl]acetamide (1)

[0181] After dissolving 56.4 g of 1-fluoro-4-nitrobenzene (0.4 mol) and51.2 g of 3-acetamidopyrrolidine (0.4 mol) in 400 ml of NMP, 66.4 g ofpotassium carbonate (0.48 mol) were added under a nitrogen atmosphereand the mixture was heated at 100° C. for 18 hours. The reaction mediumwas allowed to cool and was then poured into 2 l of water. The yellowprecipitate formed was filtered off, washed with water and then dried ina vacuum oven over P₂O₅. 100 g (100%) ofN-[1-(4-nitrophenyl)pyrrolidin-3-yl]acetamide (1) was thus obtained inthe form of a yellow solid.

Synthesis of 1-(4-nitrophenyl)pyrrolidin-4-ylamine (2)

[0182] 100 g (0.4 mol) of N-[1-(4-nitrophenyl)pyrrolidin-3-yl]acetamide(1) was placed in suspension in a solution containing 300 ml of 37%hydrochloric acid and 660 ml of water in a 2 l three-necked flask. Thereaction medium was heated at 90° C. for 7 hours 45 minutes. Aftercooling, the medium was neutralized gently with 300 ml of aqueous 35%sodium hydroxide (pH=8 approximately). The resulting solid wassubsequently filtered off and then washed with water until the washingwaters were neutral. The product was then dried under vacuum over P₂O₅.74 g (89%) of 1-(4-nitrophenyl)pyrrolidin-4-ylamine (2) was thusobtained in the form of a yellow solid.

Synthesis of N-[1-(4-nitrophenyl)pyrrolidin-3-yl]guanidine (3)

[0183] 2.07 g (0.01 mol) of [1-(4-nitrophenyl)pyrrolidin-3-yl]amine (2)was heated to 90° C. in 10 ml of DMF. 1.32 g (0.0009 mol) of 1-amidinopyrazole monohydrochloride was added slowly to the reactionmedium. The mixture was heated for 8 hours. A yellow solid was thusprecipitated. The solid thus obtained was filtered off, washed withethanol and dried under vacuum to give 2 g of a yellow powder (3) (70%).

[0184]¹H NMR (400 MHz, DMSO) ppm 8.08 (m, 2H), 6.66 (m, 2H), 4.34(m,1H), 3.72 (m, 2H), 3.56 (m, 1H), 3.48 (m, 1H), 3.33 (m, 1H), 2.31 (m,1H), 2.02 (m, 1H).

[0185] ESI+mass: m/z=250 (MH+).

Synthesis of N-[1-(4-aminophenyl)pyrrolidin-3-yl]guanidinetrihydrochloride (4)

[0186] 1.8 g (0.063 mol) of the preceding derivative (3) dissolved in 50ml of ethanol and 550 ml of water were hydrogenated in the presence ofpalladium-on-charcoal under a hydrogen pressure of 8 bar; afterfiltering off the catalyst, the expected derivative (4) was isolated inthe form of the hydrochloride (60%).

[0187]¹H NMR (400 MHz, DMSO) ppm 7.52 (m, 2H), 7.31 (m, 2H), 4.53(m,1H), 3.94 (dd,1H), 3.84 (m, 1H), 3.72 (m, 2H), 2.64 (m, 1H), 2.28 (m,1H).

[0188] ESI+mass: m/z=220 (MH+).

Example 5 3-[1-(4-Amino-phenyl)-pyrrolidin-3-yl]-thiazol-3-ium Acetate

[0189]

Synthesis of 3-[1-(4-nitrophenyl)pyrrolidin-3-yl]-1,3-thiazol-3-iummethanesulfonate (1)

[0190] 1.14 g of 1-(4-nitrophenyl)pyrrolidin-3-yl methanesulfonate(0.004 mol), 0.01 g of sodium iodate and 5 g (0.059 mol) of thiazolewere placed in a three-necked flask. The heterogeneous mixtures washeated at 110° C. for 18 hours. The reaction mixture was then pouredinto 100 ml of ethylacetate; a yellow precipitate was then obtainedwhich was filtered off and rinsed with water. After drying under vacuumin the presence of P₂O₅, 1 g of a yellow solid was obtained. Theobtained yellow solid was then recrystallized in isopropanol.

[0191] RMN 1H (400 MHz-DMSO) ppm) 10,26 (dd, 1H); 8,64 (dd ,1H); 8,41(dd 1H); 8,12 (m ,2H); 6,74 (m ,2H); 5,72 (m, 1H); 4,05 (dd ,1H); 3,95(dd, 1H); 3,76(m, 1H ); 3,62 (m, 1H); 2,76( m, 1H); 2,6 (m,1H); 2,31 (s,3H).

[0192] ESI+Mass: m/z=270[M+].

Synthesis of 3-[1-(4-Amino-phenyl)-pyrrolidin-3-yl]-thiazol-3-iumacetate (2)

[0193] After reducing with zinc/acetic acid,1-[1-(4-aminophenyl)pyrrolidin-3-yl]thyazolium chloride was obtained.

[0194] ESI+Mass: m/z=246[M+].

Example 6 1-[1-(4-aminophenyl)pyrrolidin-3-yl]pyridinium acetate

[0195]

Synthesis of 1-[1-(4-Nitro-phenyl)-pyrrolidin-3-yl]-pyridinium chloride(1)

[0196] 7 g of 1-(4-nitrophenyl)pyrrolidin-3-yl methanesulfonate (0.0244mol) and 60 ml of pyridin were placed in a three-necked flask. Themixture was heated at 100° C. for 16 hours. The precipitate was filteredoff. After washing with ether and drying, 8.5 g of a yellow powder wasobtained. The powder was solubilized in 200 ml of water, the solutionwas then passed through a IRA402 resin. After evaporating and drying,5.4 g of 1-[1-(4-nitrophenyl)pyrrolidin-3-yl]pyridinium chloride wasobtained. (1)

[0197] RMN 1H (400 MHz-DMSO) ppm 9,26 (m, 2H); 8,67 (m, 1H); 8,2 (m,2H); 8,1 (m, 2H); 6,74 (m,1H); 5,86 (m,1H); 4,03 (dd,1H); 3,84 (m, 1H);3,62 (m,1H); 2,84 (m, 1H); 2,67 (m,1H).

[0198] ESI+Mass: m/z=270[M+].

Synthesis of 1-[1-(4-Amino-phenyl)-pyrrolidin-3-yl]-pyridinium acetate(2)

[0199] After reducing with zinc/acetic acid,1-[1-(4-Amino-phenyl)-pyrrolidin-3-yl]-pyridinium acetate wasobtained.(2)

[0200] ESI+Mass: m/z=240[M+].

Example 7 1-[1-(4-Amino-phenyl)-pyrrolidin-3-yl]-4-aza-1-azonia-bicyclo[2,2,2]octane;methanesulfonate; hydrochloride

[0201]

Synthesis of1-[1-(4-nitrophenyl)pyrrolidin-3-yl]-4-aza-1-azoniabicyclo[2,2,2]octane;methanesulfonate

[0202] 4.3 g of 1-(4-nitrophenyl)pyrrolidin-3-yl methanesulfonate (0.015mol) ,15 ml of methylethylacetone and 0.56 g (0.005 mol) of 1,4diazabicyclo-2,2,2-octane were placed in a three-necked flask. Theheterogeneous mixture was heated at 95° C. for 10 hours. The reactionmixture was then poured into 150 ml of water; the mixture was filteredoff, the aqueous phase was extracted with butanol then concentrated; 0.8g of a yellow powder was thus obtained after drying corresponding to1-[1-(4-nitrophenyl)pyrrolidin-3-yl]-4-aza-1-azoniabicyclo[2,2,2]octane;methanesulfonate (1).

[0203] RMN 1H (400 MHz-DMSO) ppm 8,14 (d, 2H); 6,72 (d, 2H); 3,67-4,26(m, 4H); 3,41 (m, 7H); 3,06(m, 6H); 2,35-2,56 (m, 4H); 2,30 (s, 3H).

[0204] ESI+Mass: m/z=303[M+].

Synthesis of1-[1-(4-Amino-phenyl)-pyrrolidin-3-yl]-4-aza-1-azonia-bicyclo[2,2,2]octane;methanesulfonate; hydrochloride

[0205] 0.180 g of1-[1-(4-nitrophenyl)pyrrolidin-3-yl]-4-aza-1-azoniabicyclo[2,2,2]octane;methanesulfonate was hydrogenated under hydrogen pressure of 10 bars inthe presence of palladium-on-charcoal in ethanol. After filtrating offthe catalyst, the expected derivative (2) was isolated under thehydrochloride form.

[0206] RMN 1H (400 MHz-D₂O) ppm 7,35 (m, 2H); 6,88 (m, 2H); 4,6 (m, 1H);4,11 (t, 6H); 4,02 (m, 2H); 3,96( t, 6H); 3,74 (m, 2H); 2,8 (s, 3H);2,66 (m, 2H).

[0207] ESI+Mass: m/z=373[M+].

Example 8 [1-(4-amino-phenyl)-pyrrolidin-3-yl]-oxophosphorylcholinederivative

[0208]

[0209] The synthesis of1-(4-amino-phenyl)-pyrrolidin-3-yl]-oxophosphorylcholine derivatives wascarried out from 1-(4-Nitro-phenyl)-pyrrolidin-3-ol compound under theprotocol disclosed in S. F. Martin, J. Org. Chem. 1994, 59, 4805-4820.

Dyeing Examples Examples 1 to 20 of Dyeing Composition in an AlkalineMedium

[0210] The following compositions 1 to 20 were prepared. The amounts ofeach base and coupler are listed in moles (1×10⁻³ moles) relative to thetotal composition. Examples 1 2 3 4 5 6 7 8 9 10 11N-[1-(4-Amino-phenyl)- 10⁻³ 10⁻³ 10⁻³ 10⁻³ — — — — — — —pyrrolidin-3-yl]-guaninidine trihydrochloride (base) (mol)1′-(4-Amino-phenyl)-1-methyl- — — — — 10⁻³ 10⁻³ 10⁻³ — — — —[1,3′]bipyrrolidinyl-1-ium hydrochloride (base) (mol)3-[1-(4-Amino-3-methyl- — — — — — — — 10⁻³ 10⁻³ 10⁻³ 10⁻³phenyl)-pyrrolidin-3-yl]-1- methyl-3Himidazol-1-ium chloridehydrochloride (base) (mol) 2-(2,4-Diamino-phenoxy)- 10⁻³ — — — 10⁻³ — —10⁻³ — — — ethanol, dihydrochloride (coupler) mol3-Amino-2-chloro-6-methyl- — 10⁻³ — — — 10⁻³ — 10⁻³ — — phenol,hydrochloride (coupler)(mol) 3,6-Dimethyl-1H-pyrazolo — — 10⁻³ — — —10⁻³ — — 10⁻³ — [5,1-c] [1,2,4]triazole (coupler) (mol)2-methyl-5-aminophenol — — — 10⁻³ — — — — — — 10⁻³ (coupler)(mol) Dyeingmedium(1) (*) (*) (*) (*) (*) (*) (*) (*) (*) (*) (*) Demineralizedwater q.s. (g) 100 100 100 100 100 100 100 100 100 100 100 Examples 1213 14 15 16 17 18 19 20 1-[1-(4-Amino-phenyl)- 10⁻³ 10⁻³ 10⁻³ — — — — —— pyrrolidin-3-yl]-4-aza-1- azonia-bicyclo[2,2,2]octane methanesulfonatehydrochlorite (base) (mol) 3-[1-(4-Amino-phenyl)- — — — 10⁻³ 10⁻³ 10⁻³ —— — pyrrolidin-3-yl]-thiazol-3-ium acetate (base) (mol) 1-[1-(4- — — — —— — 10⁻³ 10⁻³ 10⁻³ aminophenyl)pyrrolidin-3- yl]pyridinium acetate(base) (mol) 2-(2,4-Diamino-phenoxy)- 10⁻³ — — 10⁻³ — — 10⁻³ — — ethanolhydrochloride (coupler) (mol) 3-Amino-2-chloro-6-methyl-phenol — 10−3 —10⁻³ — — 10⁻³ — hydrochloride (coupler) (mol)3,6-Dimethyl-1H-pyrazolo[5,1- — — 10⁻³ — — 10⁻³ — — 10⁻³ c][1,2,4]triazole (coupler) (mol) 2-methyl-5-aminophenol (coupler) — — — —— — — — — Dyeing medium (1) (*) (*) (*) (*) (*) (*) (*) (*) (*)Demineralized water q.s (g) 100 100 100 100 100 100 100 100 100 ethanolat 96° 20.8 g sodium metabisulfite in aqueous 0.23 g A.M. solution 35%diethylene-triamine-pentaacetic acid 0.48 g A.M. pentasodic salt in 40%aqueous solution C₈-C₁₀ alkylpolyglucoside in 60%  3.6 g A.M. aqueoussolution benzylic alcohol  2.0 g Polyethylene glycol 8 EO  3.0 g NH₄Cl4.32 g Aqueous ammonia comprising 20% of 2.94 g NH₃

[0211] At the time of use, the composition was mixed with an equalweight of 20-volumes aqueous hydrogen peroxide solution (6% by weight).The final pH was 9.5.

[0212] Each mixture was applied on locks of grey hair comprising 90% ofwhite hairs. After an action of time of 30 minutes, the locks wererinsed, washed with a standard shampoo, rinsed again and dried.

[0213] The following results were obtained. Examples 1 2 3 4 5 6Obtained Violet Blue Chromatic Blue Violet Violet glint blue violet RedViolet blue blue Violet Examples 7 8 9 10 11 Obtained Chromatic Violetviolet Chromatic Red glint red violet blue red violet Violet Examples 1213 14 15 16 Obtained glint blue violet Chromatic blue Blue red violetViolet Examples 17 18 19 20 Obtained glint Chromatic blue violetChromatic red violet red violet

Examples 21 to 46 of Dyeing Composition in an Acid Medium

[0214] The following compositions 21 to 46 were prepared: Examples 21 2223 24 25 26 27 28 29 30 31 32 33 34 35 N-[1-(4-Amino- 10⁻³ 10⁻³ 10⁻³10⁻³ 10⁻³ 10⁻³ — — — — — — — — — phenyl)-pyrrolidin-3- yl]-guaninidinetrihydrochloride (base) (mol) 1′-(4-Amino-phenyl)-3 — — — — — — 10⁻³10⁻³ 10⁻³ 10⁻³ — — — — — 1-methyl- [1,3′]bipyrrolidinyl-1- iumhydrochloride (base) (mol) 3-[1-(4-Amino-3- — — — — — — — — — 10⁻³ 10⁻³10⁻³ — 10⁻³ 10⁻³ methyl-phenyl)- pyrrolidin-3-yl]-1 —methyl-3Himidazol-1- ium chloride hydrochloride(base) (mol)2-(2,4-Diamino- 10⁻³ — — — — — 10⁻³ — — — 10⁻³ — — — — phenoxy)-ethanoldihydrochloride (coupler) (mol) 3-Amino-2-chloro-6- — 10⁻³ — — — — —10⁻³ — — — 10⁻³ — — — methyl-phenol hydrochloride (coupler) (mol)2-methyl-5- — — 10⁻³ — — — — — 10⁻³ — — — 10⁻³ — — aminophenol (coupler)(mol) 2-Amino-pyridin-3-ol — — — 10⁻³ — — — — — 10⁻³ — — — 10⁻³ —(coupler) (mol) 3,6-Dimethyl-1H- — — — — 10⁻³ — — — — — — — — — —pyrazolo[5,1-c] [1,2,4]triazole (coupler) (mol) 6-Hydroxy-1-H-indole — —— — — 10⁻³ — — — — — — — — 10⁻³ (coupler)(mol) Dyeing support (2) (*)(*) (*) (*) (*) (*) (*) (*) (*) (*) (*) (*) (*) (*) (*) Demineralizedwater 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 q.s.(g) Examples 36 37 38 39 40 41 42 43 44 45 46 1-[1-(4-Amino-phenyl)-10⁻³ 10⁻³ 10⁻³ 10⁻³ 10⁻³ — — — — — — pyrrolidin-3-yl]-4-aza-1-azonia-bicyclo[2,2,2]octane methanesulfonate hydrochloride (base) mol3-[1-(4-Amino-phenyl)- — — — — — 10⁻³ 10⁻³ 10⁻³ 10⁻³ — —pyrrolidin-3-yl]-thiazol-3- ium acetate (base) (mol) 1-[1-(4 — — — — — —— — — 10⁻³ 10⁻³ aminophenyl)pyrrolidin-3- yl]pyridinium acetate(base)(mol) 2-(2,4-Diamino-phenoxy)- 10⁻³ — — — — 10⁻³ — — — 10⁻³ ethanoldihydrochloride (coupler) (mol) 3-Amino-2-chloro-6- — 10⁻³ — — — — 10⁻³— — — 10⁻³ methyl-phenol hydrochloride (coupler) (mol)2-methyl-5-aminophenol — — 10⁻³ — — — — 10⁻³ — — — (coupler) (mol)2-Amino-pyridin-3-ol — — — 10⁻³ — — — — — — — (coupler) (mol)3,6-Dimethyl-1H — — — — — — — — — — pyrazolo[5,1-c] [1,2,4]triazole(coupler) (mol) 6-Hydroxy-1-H-indole — — — — 10⁻³ — — — 10⁻³ — —(coupler) (mol) Dyeing medium (2) (*) (*) (*) (*) (*) (*) (*) (*) (*)(*) (*) Demineralized water 100 100 100 100 100 100 100 100 100 100 100q.s. (g) Ethanol 96° 20.8 g Sodium metabisulfite in aqueous 0.23 g A.M.solution at 35% diethylene-triamine-pentaacetic acid 0.48 g A.M.pentasodic salt in an aqueous solution at 40% C₈-C₁₀ alkyl polyglucosidein aqueous  3.6 g A.M. solution at 60% benzylic alcohol  2.0 gPolyethylene glycol at 8 EO  3.0 g Na₂HPO₄ 0.28 g KH₂PO₄ 0.46 g

[0215] At the time of use, the composition was mixed with an equalweight of 20-volumes aqueous hydrogen peroxide solution (6% by weight).The final pH was 9.5.

[0216] Each mixture was applied on locks of grey hair comprising 90%white hairs. After an action of time of 30 minutes, the locks wererinsed, washed with a standard shampoo, rinsed again and dried.

[0217] The following results were obtained. Examples 21 22 23 24 25 26Obtained glint Violet Blue Blue Brown Red Brown Blue Violet Violetviolet Violet Violet Examples 27 28 29 30 31 32 Obtained glint Violetviolet Red Brown Violet violet blue Violet Violet blue Examples 33 34 3536 37 38 Obtained glint Red Brown Brown blue violet Red Violet VioletViolet Violet Examples 39 40 41 42 43 44 Obtained glint Brown Brown blueviolet Red Brown grey grey Violet grey Examples 45 46 Obtained glintblue violet

What is claimed is:
 1. A compound chosen from pyrrolidinyl-substitutedpara-phenylenediamine derivatives of formula (I) and the addition saltsthereof

wherein: n ranges from 0 to 4, wherein when n is greater than or equalto 2, then the radicals R₁ may be identical or different, R₁ is chosenfrom halogens; onium radicals Z; and C₁-C₆ aliphatic and alicyclic,saturated and unsaturated hydrocarbon-based chains, wherein at least onecarbon atom may be replaced with an entity chosen from an oxygen atom, anitrogen atom, a silicon atom, a sulphur atom, and a SO₂ radical; withthe proviso that the radical R₁ does not comprise a peroxide bond, adiazo radical, a nitro radical or a nitroso radical, R₂ is chosen fromonium radicals Z and radicals —X—C═NR₈—NR₉R₁₀, wherein X is chosen fromoxygen and —NR₁₁ radicals; R₈, R₉, R₁₀ and R₁₁, which may be identicalor different, are each chosen from hydrogen, C₁-C₄ alkyl radicals andC₁-C₄ hydroxyalkyl radicals; the onium radicals Z are chosen fromradicals of formulae (II), (III), and (IV): formula (II):

wherein D is a linking arm chosen from a covalent bond and linear andbranched C₁-C₁₄ alkylene chains which may be interrupted with at leastone hetero atom chosen from oxygen, sulphur and nitrogen, and which maybe substituted with at least one radical chosen from hydroxyl, C₁-C₆alkoxy and amino radicals, and which may bear at least one ketonefunctional group; R₄, R₅ and R₆, which may be identical or different,taken separately, are each chosen from C₁-C₁₅ alkyl radicals; C₁-C₆monohydroxyalkyl radicals; C₂-C₆ polyhydroxyalkyl radicals;(C₁-C₆)alkoxy(C₁-C₆)alkyl radicals; aryl radicals; benzyl radicals;C₁-C₆ amidoalkyl radicals; tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals;C₁-C₆ aminoalkyl radicals; and C₁-C₆ aminoalkyl radicals wherein theamine is mono- or disubstituted with a radical or two radicals, whichmay be identical or different, chosen from C₁-C₄ alkyl,(C₁-C₆)alkylcarbonyl, amido and (C₁-C₆)alkylsulphonyl radicals; with theproviso that when the linking arm D is a covalent bond then R₄ is chosenfrom aryl radicals; benzyl radicals; C₁-C₆ amidoalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals; C₁-C₆ aminoalkyl radicals;and C₁-C₆ aminoalkyl radicals wherein the amine is mono- ordisubstituted with a radical or two radicals, which may be identical ordifferent, chosen from C₁-C₄ alkyl, (C₁-C₆)alkylcarbonyl, amido and(C₁-C₆)alkylsulphonyl radicals, Two of the radicals chosen from R₄, R₅and R₆ form, together with the nitrogen atom to which they are attached,a saturated carbon-based cationic ring chosen from 4-, 5-, 6- and7-membered rings optionally comprising at least one hetero atom, whereinthe cationic ring may be substituted with at least one entity chosenfrom halogens, a hydroxyl radical, C₁-C₆ alkyl radicals, C₁-C₆monohydroxyalkyl radicals, C₂-C₆ polyhydroxyalkyl radicals, C₁-C₆ alkoxyradicals, tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, amido radicals,carboxyl radicals, (C₁-C₆)alkylcarbonyl radicals, thio radicals, C₁-C₆thioalkyl radicals, (C₁-C₆)alkylthio radicals, amino radicals, and aminoradicals mono- di- or tri- substituted with a radical or radicals, whichmay be identical or different, chosen from (C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl, amido and (C₁-C₆)alkylsulphonyl radicals; R₇ ischosen from C₁-C₆ alkyl radicals; C₁-C₆ monohydroxyalkyl radicals; C₂-C₆polyhydroxyalkyl radicals; aryl radicals; benzyl radicals; C₁-C₆aminoalkyl radicals; C₁-C₆ aminoalkyl radicals wherein the amine ismono- or disubstituted with a radical or two radicals, which may beidentical or different, chosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl,amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆ carboxyalkyl radicals;C₁-C₆ carbamylalkyl radicals; C₁-C₆ trifluoroalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals; C₁-C₆ sulphonamidoalkylradicals; (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radicals;N-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylsulphonamido(C₁-C₆)alkyl radicals; x is 0 or 1, when x=0,then the linking arm D is attached to the nitrogen atom bearing theradicals R₄, R₅, and R₆, when x=1, then two of the radicals chosen fromR₄, R₅, and R₆ form, together with the nitrogen atom to which they areattached, a saturated ring chosen from 5-, 6- and 7-membered rings andthe linking arm D is linked to a carbon atom of the saturated ring; andY is a counter-ion; formula (III):

wherein D is a linking arm chosen from a covalent bond and linear andbranched C₁-C₁₄ alkylene chains that may be interrupted with at leastone hetero atom chosen from oxygen, sulphur and nitrogen, and that maybe substituted with at least one radical chosen from hydroxyl, C₁-C₆alkoxy and amino radicals, and that may bear at least one ketonefunctional group; the ring members E, G, J and L, which may be identicalor different, are each chosen from carbon, oxygen, sulphur and nitrogenatoms to form, together with the ring nitrogen, a ring chosen frompyrrole, pyrazole, imidazole, triazole, oxazole, isoxazole, thiazole andisothiazole rings, q is an integer ranging from 0 to 4; o is an integerranging from 0 to 3; q+o is an integer ranging from 0 to 4; R, which maybe identical or different, is chosen from halogens, a hydroxyl radical,C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkyl radicals, C₂-C₆polyhydroxyalkyl radicals, C₁-C₆ alkoxy radicals,tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, amido radicals, carboxylradicals, C₁-C₆ alkylcarbonyl radicals, thio radicals, C₁-C₆ thioalkylradicals, (C₁-C₆)alkylthio radicals, amino radicals, amino radicalsmono- or disubstituted with a radical or two radicals, which may beidentical or different, chosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl,amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆ monohydroxyalkylradicals and C₂-C₆ polyhydroxyalkyl radicals; it being understood thatthe radical R is borne by a carbon atom, R₃, which may be identical ordifferent, is chosen from C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkylradicals, C₂-C₆ polyhydroxyalkyl radicals,tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, (C₁-C₆)alkoxy(C₁-C₆)alkylradicals, C₁-C₆ carbamylalkyl radicals, (C₁-C₆)alkylcarboxy(C₁-C₆)alkylradicals and benzyl radicals; it being understood that the radical R₃ isborne by a nitrogen atom, R₇ is chosen from C₁-C₆ alkyl radicals; C₁-C₆monohydroxyalkyl radicals; C₂-C₆ polyhydroxyalkyl radicals; arylradicals; benzyl radicals; C₁-C₆ aminoalkyl radicals; C₁-C₆ aminoalkylradicals wherein the amine is substituted with at least one radicalchosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl, amido and(C₁-C₆)alkylsulphonyl radicals; C₁-C₆ carboxyalkyl radicals; C₁-C6carbamylalkyl radicals; C₁-C₆ trifluoroalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals; C₁-C₆ sulphonamidoalkylradicals; (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;N-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylsulphonamido(C₁-C₆)alkyl radicals; x is 0 or 1 when x=0,the linking arm D is attached to the nitrogen atom, when x=1, thelinking arm D is attached to one of the ring members chosen from E, G, Jand L, and Y is a counter-ion; formula (IV):

wherein: D is a linking arm chosen from a covalent bond and linear andbranched C₁-C₁₄ alkylene chains which may be interrupted with at leastone hetero atom chosen from oxygen, sulphur and nitrogen atoms, andwhich may be substituted with at least one hydroxyl, C₁-C₆ alkoxy andamino radicals, and which may bear at least one ketone functional group;the ring members E, G, J, L and M, which may be identical or different,are each chosen from carbon, oxygen, sulphur and nitrogen atoms andform, together with the ring nitrogen, a ring chosen from pyridine,pyrimidine, pyrazine, triazine and pyridazine rings; p is an integerranging from 0 to 3; m is an integer ranging from 0 to 5; p+m is aninteger ranging from 0 to 5; R is chosen from halogens, a hydroxylradical, C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkyl radicals, C₂-C₆polyhydroxyalkyl radicals, C₁-C₆ alkoxy radicals,tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, amido radicals, carboxylradicals, C₁-C₆ alkylcarbonyl radicals, thio radicals, C₁-C₆ thioalkylradicals, (C₁-C₆)alkylthio radicals, amino radicals, amino radicalssubstituted with at least one radical chosen from (C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl, amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆monohydroxyalkyl radicals and C₂-C₆ polyhydroxyalkyl radicals; it beingunderstood that the radical R is borne by a carbon atom, R₃ is chosenfrom C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkyl radicals, C₂-C₆polyhydroxyalkyl radicals, tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals,(C₁-C₆)alkoxy(C₁-C₆)alkyl radicals, C₁-C₆ carbamylalkyl radicals,(C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals and benzyl radicals; it beingunderstood that the radical R₃ is borne by a nitrogen atom, R₇ is chosenfrom C₁-C₆ alkyl radicals; C₁-C₆ monohydroxyalkyl radicals; C₂-C₆polyhydroxyalkyl radicals; aryl radicals; benzyl radicals; C₁-C₆aminoalkyl radicals; C₁-C₆ aminoalkyl radicals wherein the amine ismono- or disubstituted with a radical or two radicals, which may beidentical or different, chosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl,amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆ carboxyalkyl radicals;C₁-C₆ carbamylalkyl radicals; C₁-C₆ trifluoroalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals; C₁-C₆ sulphonamidoalkylradicals; (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radicals;N-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylsulphonamido(C₁-C₆)alkyl radicals; x is 0 or 1 when x=0,the linking arm D is attached to the nitrogen atom, when x=1, thelinking arm D is attached to one of the ring members chosen from E, G,J, L and M, and Y is a counter-ion.
 2. The compound according to claim1, wherein, in formula (I), n is equal to
 0. 3. The compound accordingto claim 1, wherein, in formula (I), n is equal to 1 and R₁ is chosenfrom halogens and from saturated and unsaturated, aliphatic andalicyclic C₁-C₆ hydrocarbon-based chains in which at least one carbonatom may be replaced with an entity chosen from an oxygen atom, anitrogen atom, a silicon atom, a sulphur atom and an SO₂ group; with theproviso that the radical R₁ does not comprise a peroxide bond, a diazoradical, a nitro radical or a nitroso radical.
 4. The compound accordingto claim 1, wherein, in formula (I), R₁ is chosen from chlorine, bromineand C₁-C₄ alkyl, C₁-C₄ hydroxyalkyl, C₁-C₄ aminoalkyl, C₁-C₄ alkoxy andC₁-C₄ hydroxyalkoxy radicals.
 5. The compound according to claim 4,wherein R₁ is chosen from methyl, hydroxymethyl, 2-hydroxyethyl,1,2-dihydroxyethyl, methoxy, isopropyloxy and 2-hydroxyethoxy radicals.6. The compound according to claim 1, wherein, in formula (II), x isequal to 0, and R₄, R₅ and R₆, which may be identical or different,taken separately, are each chosen from C₁-C₆ alkyl radicals, C₁-C₄monohydroxyalkyl radicals, C₂-C₄ polyhydroxyalkyl radicals,(C₁-C₆)alkoxy(C₁-C₄)alkyl radicals, C₁-C₆ amidoalkyl radicals, andtri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, or R₄ and R₅ form, togetherwith the nitrogen to which they are, attached, a ring chosen fromazetidine, pyrrolidine, piperidine, piperazine and morpholine rings, andthe R₆ is chosen in this case from C₁-C₆ alkyl radicals; C₁-C₆monohydroxyalkyl radicals; C₂-C₆ polyhydroxyalkyl radicals; C₁-C₆aminoalkyl radicals; C₁-C₆ aminoalkyl radicals wherein the amine ismono- or disubstituted with a radical or two radicals, which may beidentical or different, chosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl,amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆ carbamylalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals.
 7. The compound accordingto claim 1, wherein, in formula (II), x is equal to 1, R₇ is chosen fromC₁-C₆ alkyl radicals; C₁-C₆ monohydroxyalkyl radicals; C₂-C₆polyhydroxyalkyl radicals; C₁-C₆ aminoalkyl radicals; C₁-C₆ aminoalkylradicals wherein the amine is mono- or disubstituted with a radical ortwo radicals, which may be identical or different, chosen from(C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl, amido and (C₁-C₆)alkylsulphonylradicals; C₁-C₆ carbamylalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals, R₄ and R₅ form, togetherwith the nitrogen to which they are attached, a ring chosen fromazetidine, pyrrolidine, piperidine, piperazine and morpholine rings, andthe R₆ is chosen in this case from C₁-C₆ alkyl radicals; C₁-C₆monohydroxyalkyl radicals; C₂-C₆ polyhydroxyalkyl radicals; C₁-C₆aminoalkyl radicals; C₁-C₆ aminoalkyl radicals wherein the amine ismono- or disubstituted with a radical or two radicals, which may beidentical or different, chosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl,amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆ carbamylalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals.
 8. The compound accordingto claim 1, wherein the linking arm D is chosen from a covalent bond andan alkylene, chain that may be substituted.
 9. The compound according toclaim 1, wherein, in formula (III), the ring members E, G, J and L,together with the ring nitrogen, form a ring chosen from pyrrole,imidazole, pyrazole, oxazole, thiazole and triazole rings.
 10. Thecompound according to claim 9, wherein the ring members E, G, J and L,together with the ring nitrogen, form an imidazole ring.
 11. Thecompound according to claim 1, wherein, in formula (III), x is equal to0 and the linking arm D is chosen from a covalent bond and an alkylenechain that is substituted.
 12. The compound according to claim 1,wherein, in formula (IV), the ring members E, G, J, L and M form, withthe ring nitrogen, a ring chosen from pyridine and pyrimidine rings. 13.The compound according to claim 1, wherein, in formula (IV), x is equalto 0, and R is chosen from a hydroxyl radical, C₁-C₆ alkyl radicals,C₁-C₆ monohydroxyalkyl radicals, C₂-C₆ polyhydroxyalkyl radicals, C₁-C₆alkoxy radicals, tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, amidoradicals, C₁-C₆ alkylcarbonyl radicals, amino radicals, amino radicalsmono- or disubstituted with a radical or two radicals, which may beidentical or different, chosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl,amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆ monohydroxyalkylradicals and C₂-C₆ polyhydroxyalkyl radicals, and R₃ is chosen fromC₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkyl radicals, C₂-C₆polyhydroxyalkyl radicals, tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals,(C₁-C₆)alkoxy(C₁-C₆)alkyl radicals and C₁-C₆ carbamylalkyl radicals. 14.The compound according to claim 1, wherein, in formula (IV), x is equalto 1, R₇ is chosen from C₁-C₆ alkyl radicals; C₁-C₆ monohydroxyalkylradicals; C₂-C₆ polyhydroxyalkyl radicals; C₁-C₆ aminoalkyl radicals;C₁-C₆ aminoalkyl radicals wherein the amine is mono- or disubstitutedwith a radical or two radicals, which may be identical or different,chosen from (C₁-C₆)alkyl radicals, (C₁-C₆)alkylcarbonyl radicals, amidoradicals and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆ carbamylalkylradicals; tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals; R is chosen from a hydroxylradical, C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkyl radicals, C₂-C₆polyhydroxyalkyl radicals, C₁-C₆ alkoxy radicals,tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, amido radicals, C₁-C₆alkylcarbonyl radicals, amino radicals, amino radicals mono- ordisubstituted with a radical or two radicals, which may be identical ordifferent, chosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl, amido and(C₁-C₆)alkylsulphonyl radicals; and R₃ is chosen from C₁-C₆ alkylradicals, C₁-C₆ monohydroxyalkyl radicals, C₂-C₆ polyhydroxyalkylradicals, tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals,(C₁-C₆)alkoxy(C₁-C₆)alkyl radicals and C₁-C₆ carbamylalkyl radicals. 15.The compound according to claim 1, wherein, in formula (III) or (IV), R,R₇ and R₃ are alkyl radicals that may be substituted.
 16. The compoundaccording to claim 1, wherein, in formula (I), R₂ is a radical—X—C═NR₈—NR₉R₁₀, wherein X is chosen from oxygen and a radical —NR₁₁;R₈, R₉, R₁₀ and R₁₁, which may be identical or different, are eachchosen from hydrogen, C₁-C₄ alkyl radicals and hydroxyalkyl radicals.17. The compound according to claim 16, wherein X is a radical —NR₁₁, R₈is a hydrogen, and R₉ and R₁₀, which may be identical or different, areeach chosen from hydrogen and alkyl radicals.
 18. The compound accordingto claim 1, wherein, in formula (I), the R₂ is chosen from radicals—XP(O)(O—)OCH₂CH₂N⁺(CH₃)₃ wherein X is chosen from oxygen and radicals—NR₁₁, wherein R₁₁ is chosen from hydrogen, C₁-C₄ alkyl radicals andhydroxyalkyl radicals.
 19. The compound according to claim 1, whereinsaid compound is chosen from:N′-[1-(4-Aminophenyl)pyrrolidin-3-yl]-N,N-dimethylguanidine,N-[1-(4-Aminophenyl)pyrrolidin-3-yl]guanidine,3-[1-(4-Aminophenyl)pyrrolidin-3-yl]-1-methyl-3H-imidazol-1-iumchloride,[1-(4-Aminophenyl)pyrrolidin-3-yl]dimethyl-(3-trimethylsilanylpropyl)ammoniumchloride,N′-[1-(4-Amino-3-methylphenyl)pyrrolidin-3-yl]-N,N-dimethylguanidine,N-[1-(4-Amino-3-methylphenyl)pyrrolidin-3-yl]guanidine,3-[1-(4-Amino-3-methylphenyl)pyrrolidin-3-yl]-1-methyl-3H-imidazol-1-iumchloride,[1-(4-Amino-3-methylphenyl)pyrrolidin-3-yl]dimethyl-(3-trimethylsilanylpropyl)ammoniumchloride,3-[1-(4-Aminophenyl)pyrrolidin-3-yl]-1-(3-trimethylsilanylpropyl)-3H-imidazol-1-iumchloride,3-[1-(4-Amino-3-methylphenyl)pyrrolidin-3-yl]-1-(3-trimethylsilanylpropyl)-3H-imidazol-1-iumchloride, 1′-(4-Aminophenyl)-1-methyl-[1,3′]bipyrrolidinyl-1-iumchloride,1′-(4-Amino-3-methylphenyl)-1-methyl-[1,3′]bipyrrolidinyl-1-iumchloride,3-{[1-(4-Aminophenyl)pyrrolidin-3-ylcarbamoyl]methyl}-1-methyl-3H-imidazol-1-iumchloride,3-{[1-(4-Amino-3-methylphenyl)pyrrolidin-3-ylcarbamoyl]methyl}-1-methyl-3H-imidazol-1-iumchloride, and 1′-(4-amino-phenyl)-1-methyl-[1,3′]bipyrrolidinyl-1-iumchloride.
 20. The compound according to claim 19, wherein said compoundis chosen from1-methyl-3-[1-(4-aminophenyl)pyrrolidin-3-yl]-3H-imidazol-1-ium chloridehydrochloride; N-[1-(4-aminophenyl)pyrrolidin-3-yl]guanidinetrihydrochloride, and1′-(4-amino-phenyl)-1-methyl-[1,3′]bipyrrolidinyl-1-ium chloride. 21.The compound according to claim 1, wherein the linking arm D comprises aphosphoryl radical.
 22. The compound according to claim 21, wherein thelinking arm D is chosen from[1-(4-Amino-phenyl)-pyrrolidin-3-yl]-oxophosphorylcholine and[1-(4-Amino-3-methylphenyl)-pyrrolidin-3-yl]-oxophosphorylcholine.
 23. Adye composition comprising at least one oxidation base chosen frompyrrolidinyl-substituted para-phenylenediamine derivatives of formula(I) and the addition salts thereof:

wherein: n ranges from 0 to 4, wherein when n is greater than or equalto 2, then the radicals R₁ may be identical or different, R₁ is chosenfrom halogens; onium radicals Z; and C₁-C₆ aliphatic and alicyclic,saturated and unsaturated hydrocarbon-based chains wherein at least onecarbon atom may be replaced with an entity chosen from an oxygen atom, anitrogen atom, a silicon atom, a sulphur atom, and a SO₂ radical withthe proviso that the radical R₁ does not comprise a peroxide bond, adiazo radical, a nitro radical or a nitroso radical, R₂ is chosen fromonium radicals Z and radicals —X—C═NR₈—NR₉R₁₀, wherein the X is chosenfrom oxygen and —NR₁₁ radicals; R₈, R₉, R₁₀ and R₁₁, which may beidentical or different, are each chosen from hydrogen, C₁-C₄ alkylradicals and C₁-C₄ hydroxyalkyl radicals; the onium radicals Z arechosen from radicals of formulae (II), (III), and (IV): formula (II):

wherein D is a linking arm chosen from a covalent bond and linear andbranched C₁-C₁₄ alkylene chains which may be interrupted with at leastone hetero atom chosen from oxygen, sulphur and nitrogen, and which maybe substituted with at least one radical chosen from hydroxyl, C₁-C₆alkoxy and amino radicals, and which may bear at least one ketonefunctional group; R₄, R₅ and R₆, which may be identical or different,taken separately, are each chosen from C₁-C₁₅ alkyl radicals; C₁-C₆monohydroxyalkyl radicals; C₂-C₆ polyhydroxyalkyl radicals;(C₁-C₆)alkoxy(C₁-C₆)alkyl radicals; aryl radicals; benzyl radicals;C₁-C₆ amidoalkyl radicals; tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals;C₁-C₆ aminoalkyl radicals; and C₁-C₆ aminoalkyl radicals wherein theamine is mono- or disubstituted with a radical or two radicals, whichmay be identical or different, chosen from C₁-C₄ alkyl,(C₁-C₆)alkylcarbonyl, amido and (C,-C₆)alkylsulphonyl radicals; with theproviso that when the linking arm D is a covalent bond then R₄ is chosenfrom aryl radicals; benzyl radicals; C₁-C₆ amidoalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals; C₁-C₆ aminoalkyl radicals;and C₁-C₆ aminoalkyl radicals wherein the amine is mono- ordisubstituted with a radical or two radicals, which may be identical ordifferent, chosen from C₁-C₄ alkyl, (C₁-C₆)alkylcarbonyl, amido and(C₁-C₆)alkylsulphonyl radicals; Two of the radicals chosen from R₄, R₅and R₆ form, together with the nitrogen atom to which they are attached,a saturated carbon-based cationic ring chosen from 4-, 5-, 6- and7-membered rings optionally comprising at least one hetero atom whereinthe cationic ring may be substituted with at least one entity chosenfrom halogens, a hydroxyl radical, C₁-C₆ alkyl radicals, C₁-C₆monohydroxyalkyl radicals, C₂-C₆ polyhydroxyalkyl radicals, C₁-C₆ alkoxyradicals, tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, amido radicals,carboxyl radicals, (C₁-C₆)alkylcarbonyl radicals, thio radicals, C₁-C₆thioalkyl radicals, (C₁-C₆)alkylthio radicals, amino radicals, and aminoradicals mono- di- or tri- substituted with a radical or radicals, whichmay be identical or different, chosen from (C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl, amido and (C₁-C₆)alkylsulphonyl radicals; R₇ ischosen from C₁-C₆ alkyl radicals; C₁-C₆ monohydroxyalkyl radicals; C₂-C₆polyhydroxyalkyl radicals; aryl radicals; benzyl radicals; C₁-C₆aminoalkyl radicals; C₁-C₆ aminoalkyl radicals wherein the amine ismono- or disubstituted with a radical or two radicals, which may beidentical or different, chosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl,amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆ carboxyalkyl radicals;C₁-C₆ carbamylalkyl radicals; C₁-C₆ trifluoroalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals; C₁-C₆ sulphonamidoalkylradicals; (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radicals;N-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylsulphonamido(C₁-C₆)alkyl radicals; x is 0 or 1, when x=0,then the linking arm D is attached to the nitrogen atom bearing theradicals R₄, R₅, and R₆, when x=1, then two of the radicals chosen fromR₄, R₅, and R₆ form, together with the nitrogen atom to which they areattached, a saturated ring chosen from 5-, 6- and 7-membered rings andthe linking arm D is linked to a carbon atom of the saturated ring; andY is a counter-ion; formula (III):

wherein D is a linking arm chosen from a covalent bond and linear andbranched C₁-C₁₄ alkylene chains that may be interrupted with at leastone hetero atom chosen from oxygen, sulphur and nitrogen, and that maybe substituted with at least one radical chosen from hydroxyl, C₁-C₆alkoxy and amino radicals, and that may bear at least one ketonefunctional group; the ring members E, G, J and L, which may be identicalor different, are each chosen from carbon, oxygen, sulphur and nitrogenatoms to form, together with the ring nitrogen, a ring chosen frompyrrole, pyrazole, imidazole, triazole, oxazole, isoxazole, thiazole andisothiazole rings; q is an integer ranging from 0 to 4; o is an integerranging from 0 to 3; q+o is an integer ranging from 0 to 4; R, which maybe identical or different, is chosen from halogens, a hydroxyl radical,C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkyl radicals, C₂-C₆polyhydroxyalkyl radicals, C₁-C₆ alkoxy radicals,tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, amido radicals, carboxylradicals, C₁-C₆ alkylcarbonyl radicals, thio radicals, C₁-C₆ thioalkylradicals, (C₁-C₆)alkylthio radicals, amino radicals, amino radicalsmono- or disubstituted with a radical or two radicals, which may beidentical or different, chosen from (C₁-C₆)alkyl, (C₁-C6)alkylcarbonyl,amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆ monohydroxyalkylradicals and C₂-C₆ polyhydroxyalkyl radicals; it being understood thatthe radical R is borne by a carbon atom, R₃, which may be identical ordifferent, is chosen from C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkylradicals, C₂-C₆ polyhydroxyalkyl radicals,tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, (C₁-C₆)alkoxy(C₁-C₆)alkylradicals, C₁-C₆ carbamylalkyl radicals, (C₁-C6)alkylcarboxy(C₁-C₆)alkylradicals and benzyl radicals; it being understood that the radical R₃ isborne by a nitrogen atom, R₇ is chosen from C₁-C₆ alkyl radicals; C₁-C₆monohydroxyalkyl radicals; C₂-C₆ polyhydroxyalkyl radicals; arylradicals; benzyl radicals; C₁-C₆ aminoalkyl radicals; C₁-C₆ aminoalkylradicals wherein the amine is substituted with at least one radicalchosen from (C₁-C₆)alkyl, (C₁-C6)alkylcarbonyl, amido and(C₁-C₆)alkylsulphonyl radicals; C₁-C₆ carboxyalkyl radicals; C₁-C₆carbamylalkyl radicals; C₁-C₆ trifluoroalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals; C₁-C₆ sulphonamidoalkylradicals; (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;N-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylsulphonamido(C₁-C₆)alkyl radicals; x is 0 or 1 when x=0,the linking arm D is attached to the nitrogen atom, when x=1, thelinking arm D is attached to one of the ring members chosen from E, G, Jand L, and Y is a counter-ion; formula (IV):

wherein: D is a linking arm chosen from a covalent bond and linear andbranched C₁-C₁₄ alkylene chains which may be interrupted with at leastone hetero atom chosen from oxygen, sulphur and nitrogen atoms, andwhich may be substituted with at least one hydroxyl, C₁-C₆ alkoxy andamino radicals, and which may bear at least one ketone functional group;the ring members E, G, J, L and M, which may be identical or different,are each chosen from carbon, oxygen, sulphur and nitrogen atoms andform, together with the ring nitrogen, a ring chosen from pyridine,pyrimidine, pyrazine, triazine and pyridazine rings; p is an integerranging from 0 to 3; m is an integer ranging from 0 to 5; p+m is aninteger ranging from 0 to 5; R is chosen from halogens, a hydroxylradical, C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkyl radicals, C₂-C₆polyhydroxyalkyl radicals, C₁-C₆ alkoxy radicals,tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, amido radicals, carboxylradicals, C₁-C₆ alkylcarbonyl radicals, thio radicals, C₁-C₆ thioalkylradicals, (C₁-C₆)alkylthio radicals, amino radicals, amino radicalssubstituted with at least one radical chosen from (C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl, amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆monohydroxyalkyl radicals and C₂-C₆ polyhydroxyalkyl radicals; it beingunderstood that the radical R is borne by a carbon atom, R₃ is chosenfrom C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkyl radicals, C₂-C₆polyhydroxyalkyl radicals, tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals,(C₁-C₆)alkoxy(C₁-C₆)alkyl radicals, C₁-C₆ carbamylalkyl radicals,(C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals and benzyl radicals; it beingunderstood that the radical R₃ is borne by a nitrogen atom, R₇ is chosenfrom C₁-C₆ alkyl radicals; C₁-C₆ monohydroxyalkyl radicals; C₂-C₆polyhydroxyalkyl radicals; aryl radicals; benzyl radicals; C₁-C₆aminoalkyl radicals; C₁-C₆ aminoalkyl radicals wherein the amine ismono- or disubstituted with a radical or two radicals, which may beidentical or different, chosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl,amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆ carboxyalkyl radicals;C₁-C₆ carbamylalkyl radicals; C₁-C₆ trifluoroalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals; C₁-C₆ sulphonamidoalkylradicals; (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radicals;N-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylsulphonamido(C₁-C₆)alkyl radicals; x is 0 or 1 when x=0,the linking arm D is attached to the nitrogen atom, when x=1, thelinking arm D is attached to one of the ring members chosen from E, G.J, L and M, and Y is a counter-ion.
 24. The composition according toclaim 23, further comprising at least one coupler chosen frommeta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthaleniccouplers and heterocyclic couplers, and the addition salts thereof. 25.The composition according to claim 23, further comprising at least oneadditional oxidation base, other than the at least one oxidation basechosen from pyrrolidinyl-substituted para-phenylenediamine derivativesof formula (I) and the addition salts thereof, chosen frompara-phenylenediamines, bis(phenyl)alkylenediamines, para-aminophenols,ortho-aminophenols and heterocyclic bases, and the addition saltsthereof.
 26. The composition according to claim 23, wherein the amountof the at least one oxidation base ranges from 0.001% to 10% by weight,relative to the total weight of the dye composition.
 27. The compositionaccording to claim 25, wherein the amount of the at least one additionaloxidation base ranges from 0.001% to 10% by weight, relative to thetotal weight of the composition.
 28. The composition according to claim24, wherein the amount of the at least one coupler ranges from 0.001% to10% by weight, relative to the total weight of the dye composition. 29.The composition according to claim 23, further comprising at least onedirect dye chosen from nitrobenzene, azo, and methine direct dyes.
 30. Aprocess for oxidation dyeing of keratin fibers, comprising applying tothe keratin fibers at least one dye composition comprising, in a mediumsuitable for dyeing, at least one oxidation base chosen frompyrrolidinyl-substituted para-phenylenediamine derivatives of formula(I) and the addition salts thereof:

wherein: n ranges from 0 to 4, wherein when n is greater than or equalto 2, then the radicals R₁ may be identical or different, R₁ is chosenfrom halogens; onium radicals Z; and C₁-C₆ aliphatic and alicyclic,saturated and unsaturated hydrocarbon-based chains wherein at least onecarbon atom may be replaced with an entity chosen from an oxygen atom, anitrogen atom, a silicon atom, a sulphur atom, and a SO₂ radical, withthe proviso that the radical R₁ does not comprise a peroxide bond, adiazo radical, a nitro radical or a nitroso radical, R₂ is chosen fromonium radicals Z and radicals —X—C═NR₈—NR₉R₁₀, wherein the X is chosenfrom oxygen and —NR₁₁ radicals; R₈, R₉, R₁₀ and R₁₁, which may beidentical or different, are each chosen from hydrogen, C₁-C₄ alkylradicals and C₁-C₄ hydroxyalkyl radicals; the onium radicals Z arechosen from radicals of formulae (II), (III), and (IV): formula (II):

wherein D is a linking arm chosen from a covalent bond and linear andbranched C₁-C₁₄ alkylene chains which may be interrupted with at leastone hetero atom chosen from oxygen, sulphur and nitrogen, and which maybe substituted with at least one radical chosen from hydroxyl, C₁-C₆alkoxy and amino radicals, and which may bear at least one ketonefunctional group; R₄, R₅ and R₆, which may be identical or different,taken separately, are each chosen from C₁-C₁₅ alkyl radicals; C₁-C₆monohydroxyalkyl radicals; C₂-C₆ polyhydroxyalkyl radicals;(C₁-C₆)alkoxy(C₁-C₆)alkyl radicals; aryl radicals; benzyl radicals;C₁-C₆ amidoalkyl radicals; tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals;C₁-C₆ aminoalkyl radicals; and C₁-C₆ aminoalkyl radicals wherein theamine is mono- or disubstituted with a radical or two radicals, whichmay be identical or different, chosen from C₁-C₄ alkyl,(C₁-C₆)alkylcarbonyl, amido and (C₁-C₆)alkylsulphonyl radicals; with theproviso that when the linking arm D is a covalent bond then R₄ is chosenfrom aryl radicals; benzyl radicals; C₁-C₆ amidoalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals; C₁-C₆ aminoalkyl radicals;and C₁-C₆ aminoalkyl radicals wherein the amine is mono- ordisubstituted with a radical or two radicals, which may be identical ordifferent, chosen from C₁-C₄ alkyl, (C₁-C₆)alkylcarbonyl, amido and(C₁-C₆)alkylsulphonyl radicals; Two of the radicals chosen from R₄, R₅and R₆ form, together with the nitrogen atom to which they are attached,a saturated carbon-based cationic ring chosen from 4-, 5-, 6- and7-membered rings optionally comprising at least one hetero atom, whereinthe cationic ring may be substituted with at least one entity chosenfrom halogens, a hydroxyl radical, C₁-C₆ alkyl radicals, C₁-C₆monohydroxyalkyl radicals, C₂-C₆ polyhydroxyalkyl radicals, C₁-C₆ alkoxyradicals, tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, amido radicals,carboxyl radicals, (C₁-C₆)alkylcarbonyl radicals, thio radicals, C₁-C₆thioalkyl radicals, (C₁-C₆)alkylthio radicals, amino radicals, and aminoradicals mono- di- or tri- substituted with a radical or radicals, whichmay be identical or different, chosen from (C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl, amido and (C₁-C₆)alkylsulphonyl radicals; R₇ ischosen from C₁-C₆ alkyl radicals; C₁-C₆ monohydroxyalkyl radicals; C₂-C₆polyhydroxyalkyl radicals; aryl radicals; benzyl radicals; C₁-C₆aminoalkyl radicals; C₁-C₆ aminoalkyl radicals wherein the amine ismono- or disubstituted with a radical or two radicals, which may beidentical or different, chosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl,amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆ carboxyalkyl radicals;C₁-C₆ carbamylalkyl radicals; C₁-C₆ trifluoroalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals; C₁-C₆ sulphonamidoalkylradicals; (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radicals;N-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylsulphonamido(C₁-C₆)alkyl radicals; x is 0 or 1, when x=0,then the linking arm D is attached to the nitrogen atom bearing theradicals R₄, R₅, and R₆, when x=1, then two of the radicals chosen fromR₄, R₅, and R₆ form, together with the nitrogen atom to which they areattached, a saturated ring chosen from 5-, 6- and 7-membered rings andthe linking arm D is linked to a carbon atom of the saturated ring; andY is a counter-ion; formula (III):

wherein D is a linking arm chosen from a covalent bond and linear andbranched C₁-C₁₄ alkylene chains that may be interrupted with at leastone hetero atom chosen from oxygen, sulphur and nitrogen, and that maybe substituted with at least one radical chosen from hydroxyl, C₁-C₆alkoxy and amino radicals, and that may bear at least one ketonefunctional group; the ring members E, G, J and L, which may be identicalor different, are each chosen from carbon, oxygen, sulphur and nitrogenatoms to form, together with the ring nitrogen, a ring chosen frompyrrole, pyrazole, imidazole, triazole, oxazole, isoxazole, thiazole andisothiazole rings; q is an integer ranging from 0 to 4; o is an integerranging from 0 to 3; q+o is an integer ranging from 0 to 4; R, which maybe identical or different, is chosen from halogens, a hydroxyl radical,C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkyl radicals, C₂-C₆polyhydroxyalkyl radicals, C₁-C₆ alkoxy radicals,tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, amido radicals, carboxylradicals, C₁-C₆ alkylcarbonyl radicals, thio radicals, C₁-C₆ thioalkylradicals, (C₁-C₆)alkylthio radicals, amino radicals, amino radicalsmono- or disubstituted with a radical or two radicals, which may beidentical or different, chosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl,amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆ monohydroxyalkylradicals and C₂-C₆ polyhydroxyalkyl radicals; it being understood thatthe radical R is borne by a carbon atom, R₃, which may be identical ordifferent, is chosen from C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkylradicals, C₂-C₆ polyhydroxyalkyl radicals,tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, (C₁-C₆)alkoxy(C₁-C₆)alkylradicals, C₁-C₆ carbamylalkyl radicals, (C₁-C₆)alkylcarboxy(C₁-C₆)alkylradicals and benzyl radicals; it being understood that the radical R₃ isborne by a nitrogen atom, R₇ is chosen from C₁-C₆ alkyl radicals; C₁-C₆monohydroxyalkyl radicals; C₂-C₆ polyhydroxyalkyl radicals; arylradicals; benzyl radicals; C₁-C₆ aminoalkyl radicals; C₁-C₆ aminoalkylradicals wherein the amine is substituted with at least one radicalchosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl, amido and(C₁-C₆)alkylsulphonyl radicals; C₁-C₆ carboxyalkyl radicals; C₁-C₆carbamylalkyl radicals; C₁-C₆ trifluoroalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals; C₁-C₆ sulphonamidoalkylradicals; (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;N-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylsulphonamido(C₁-C₆)alkyl radicals; x is 0 or 1 when x=0,the linking arm D is attached to the nitrogen atom, when x=1, thelinking arm D is attached to one of the ring members chosen from E, G, Jand L, and Y is a counter-ion; formula (IV):

wherein: D is a linking arm chosen from a covalent bond and linear andbranched C₁-C₁₄ alkylene chains which may be interrupted with at leastone hetero atom chosen from oxygen, sulphur and nitrogen atoms, andwhich may be substituted with at least one hydroxyl, C₁-C₆ alkoxy andamino radicals, and which may bear at least one ketone functional group;the ring members E, G, J, L and M, which may be identical or different,are each chosen from carbon, oxygen, sulphur and nitrogen atoms andform, together with the ring nitrogen, a ring chosen from pyridine,pyrimidine, pyrazine, triazine and pyridazine rings; p is an integerranging from 0 to 3; m is an integer ranging from 0 to 5; p+m is aninteger ranging from 0 to 5; R is chosen from halogens, a hydroxylradical, C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkyl radicals, C₂-C₆polyhydroxyalkyl radicals, C₁-C₆ alkoxy radicals,tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, amido radicals, carboxylradicals, C₁-C₆ alkylcarbonyl radicals, thio radicals, C₁-C₆ thioalkylradicals, (C₁-C₆)alkylthio radicals, amino radicals, amino radicalssubstituted with at least one radical chosen from (C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl, amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆monohydroxyalkyl radicals and C₂-C₆ polyhydroxyalkyl radicals; it beingunderstood that the radical R is borne by a carbon atom, R₃ is chosenfrom C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkyl radicals, C₂-C₆polyhydroxyalkyl radicals, tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals,(C₁-C₆)alkoxy(C₁-C₆)alkyl radicals, C₁-C₆ carbamylalkyl radicals,(C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals and benzyl radicals; it beingunderstood that the radical R₃ is borne by a nitrogen atom, R₇ is chosenfrom C₁-C₆ alkyl radicals; C₁-C₆ monohydroxyalkyl radicals; C₂-C₆polyhydroxyalkyl radicals; aryl radicals; benzyl radicals; C₁-C₆aminoalkyl radicals; C₁-C₆ aminoalkyl radicals wherein the amine ismono- or disubstituted with a radical or two radicals, which may beidentical or different, chosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl,amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆ carboxyalkyl radicals;C₁-C₆ carbamylalkyl radicals; C₁-C₆ trifluoroalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals; C₁-C₆ sulphonamidoalkylradicals; (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radicals;N-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylsulphonamido(C₁-C₆)alkyl radicals; x is 0 or 1 when x=0,the linking arm D is attached to the nitrogen atom, when x=1, thelinking arm D is attached to one of the ring members chosen from E, G,J, L and M, and Y is a counter-ion; and developing color using at leastone oxidizing agent.
 31. The process according to claim 30, wherein theat least one oxidizing agent is chosen from hydrogen peroxide, ureaperoxide, alkali metal bromates, persalts, peracids and oxidase enzymes.32. The process according to claim 31, wherein the at least oneoxidizing agent is hydrogen peroxide.
 33. The process according to claim30, comprising mixing, at the time of use, the at least one oxidizingagent with the at least one dye composition,
 34. The process accordingto claim 30, comprising applying to the keratin fibers at least oneoxidizing composition comprising, in a medium suitable for dyeing, theat least one oxidizing agent, simultaneously with or sequentially to theat least one dye composition, in a medium suitable for dyeing.
 35. Amulti-compartment kit or device, comprising a first compartmentcomprising a dye composition comprising, in a medium suitable fordyeing, at least one oxidation base chosen from pyrrolidinyl-substitutedpara-phenylenediamine derivatives of formula (I) and the addition saltsthereof

wherein: n ranges from 0 to 4, wherein when n is greater than or equalto 2, then the radicals R₁ may be identical or different, R₁ is chosenfrom halogens; onium radicals Z; and C₁-C₆ aliphatic and alicyclic,saturated and unsaturated hydrocarbon-based chains wherein at least onecarbon atom may be replaced with an entity chosen from an oxygen atom, anitrogen atom, a silicon atom, a sulphur atom, and a SO₂ radical, withthe proviso that the radical R₁ does not comprise a peroxide bond, adiazo radical, a nitro radical or a nitroso radical, R₂ is chosen fromonium radicals Z and radicals —X—C═NR₈—NR₉R₁₀, wherein the X is chosenfrom oxygen and —NR₁₁ radicals; R₈, R₉, R₁₀ and R₁₁, which may beidentical or different, are each chosen from hydrogen, C₁-C₄ alkylradicals and C₁-C₄ hydroxyalkyl radicals; the onium radicals Z arechosen from radicals of formulae (II), (III), and (IV): formula (II):

wherein D is a linking arm chosen from a covalent bond and linear andbranched C₁-C₁₄ alkylene chains which may be interrupted with at leastone hetero atom chosen from oxygen, sulphur and nitrogen, and which maybe substituted with at least one radical chosen from hydroxyl, C₁-C₆alkoxy and amino radicals, and which may bear at least one ketonefunctional group; R₄, R₅ and R₆, which may be identical or different,taken separately, are each chosen from C₁-C₁₅ alkyl radicals; C₁-C₆monohydroxyalkyl radicals; C₂-C₆ polyhydroxyalkyl radicals;(C₁-C₆)alkoxy(C₁-C₆)alkyl radicals; aryl radicals; benzyl radicals;C₁-C₆ amidoalkyl radicals; tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals;C₁-C₆ aminoalkyl radicals; and C₁-C₆ aminoalkyl radicals wherein theamine is mono- or disubstituted with a radical or two radicals, whichmay be identical or different, chosen from C₁-C₄ alkyl,(C₁-C₆)alkylcarbonyl, amido and (C₁-C₆)alkylsulphonyl radicals; with theproviso that when the linking arm D is a covalent bond then R₄ is chosenfrom aryl radicals; benzyl radicals; C₁-C₆ amidoalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals; C₁-C₆ aminoalkyl radicals;and C₁-C₆ aminoalkyl radicals wherein the amine is mono- ordisubstituted with a radical or two radicals, which may be identical ordifferent, chosen from C₁-C₄ alkyl, (C₁-C₆)alkylcarbonyl, amido and(C₁-C₆)alkylsulphonyl radicals, Two of the radicals chosen from R₄, R₅and R₆ form, together with the nitrogen atom to which they are attached,a saturated carbon-based cationic ring chosen from 4-, 5-, 6- and7-membered rings optionally comprising at least one hetero atom, whereinthe cationic ring may be substituted with at least one entity chosenfrom halogens, a hydroxyl radical, C₁-C₆ alkyl radicals, C₁-C₆monohydroxyalkyl radicals, C₂-C₆ polyhydroxyalkyl radicals, C₁-C₆ alkoxyradicals, tri(C₁-₆)alkylsilane(C₁-C₆)alkyl radicals, amido radicals,carboxyl radicals, (C₁-C₆)alkylcarbonyl radicals, thio radicals, C₁-C₆thioalkyl radicals, (C₁-C₆)alkylthio radicals, amino radicals, and aminoradicals mono- di- or tri- substituted with a radical or radicals, whichmay be identical or different, chosen from (C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl, amido and (C₁-C₆)alkylsulphonyl radicals; R₇ ischosen from C₁-C₆ alkyl radicals; C₁-C₆ monohydroxyalkyl radicals; C₂-C₆polyhydroxyalkyl radicals; aryl radicals; benzyl radicals; C₁-C₆aminoalkyl radicals; C₁-C₆ aminoalkyl radicals wherein the amine ismono- or disubstituted with a radical or two radicals, which may beidentical or different, chosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl,amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆ carboxyalkyl radicals;C₁-C₆ carbamylalkyl radicals; C₁-C₆ trifluoroalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals; C₁-C₆ sulphonamidoalkylradicals; (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radicals;N-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylsulphonamido(C₁-C₆)alkyl radicals; x is 0 or 1, when x=0,then the linking arm D is attached to the nitrogen atom bearing theradicals R₄, R₅, and R₆, when x=1, then two of the radicals chosen fromR₄, R₅, and R₆ form, together with the nitrogen atom to which they areattached, a saturated ring chosen from 5-, 6- and 7-membered rings andthe linking arm D is linked to a carbon atom of the saturated ring; andY is a counter-ion; formula (III):

wherein D is a linking arm chosen from a covalent bond and linear andbranched C₁-C₁₄ alkylene chains that may be interrupted with at leastone hetero atom chosen from oxygen, sulphur and nitrogen, and that maybe substituted with at least one radical chosen from hydroxyl, C₁-C₆alkoxy and amino radicals, and that may bear at least one ketonefunctional group; the ring members E, G, J and L, which may be identicalor different, are each chosen from carbon, oxygen, sulphur and nitrogenatoms to form, together with the ring nitrogen, a ring chosen frompyrrole, pyrazole, imidazole, triazole, oxazole, isoxazole, thiazole andisothiazole rings, q is an integer ranging from 0 to 4; o is an integerranging from 0 to 3; q+o is an integer ranging from 0 to 4; R, which maybe identical or different, is chosen from halogens, a hydroxyl radical,C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkyl radicals, C₂-C₆polyhydroxyalkyl radicals, C₁-C₆ alkoxy radicals,tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, amido radicals, carboxylradicals, C₁-C₆ alkylcarbonyl radicals, thio radicals, C₁-C₆ thioalkylradicals, (C₁-C₆)alkylthio radicals, amino radicals, amino radicalsmono- or disubstituted with a radical or two radicals, which may beidentical or different, chosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl,amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆ monohydroxyalkylradicals and C₂-C₆ polyhydroxyalkyl radicals; it being understood thatthe radical R is borne by a carbon atom, R₃, which may be identical ordifferent, is chosen from C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkylradicals, C₂-C₆ polyhydroxyalkyl radicals,tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, (C₁-C₆)alkoxy(C₁-C₆)alkylradicals, C₁-C₆ carbamylalkyl radicals, (C₁-C₆)alkylcarboxy(C₁-C₆)alkylradicals and benzyl radicals; it being understood that the radical R₃ isborne by a nitrogen atom, R₇ is chosen from C₁-C₆ alkyl radicals; C₁-C₆monohydroxyalkyl radicals; C₂-C₆ polyhydroxyalkyl radicals; arylradicals; benzyl radicals; C₁-C₆ aminoalkyl radicals; C₁-C₆ aminoalkylradicals wherein the amine is substituted with at least one radicalchosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl, amido and(C₁-C₆)alkylsulphonyl radicals; C₁-C₆ carboxyalkyl radicals; C₁-C₆carbamylalkyl radicals; C₁-C₆ trifluoroalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals; C₁-C₆ sulphonamidoalkylradicals; (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;N-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylsulphonamido(C₁-C₆)alkyl radicals; x is 0 or 1 when x=0,the linking arm D is attached to the nitrogen atom, when x=1, thelinking arm D is attached to one of the ring members chosen from E, G, Jand L, and Y is a counter-ion; formula (IV):

wherein: D is a linking arm chosen from a covalent bond and linear andbranched C₁-C₁₄ alkylene chains which may be interrupted with at leastone hetero atom chosen from oxygen, sulphur and nitrogen atoms, andwhich may be substituted with at least one hydroxyl, C₁-C₆ alkoxy andamino radicals, and which may bear at least one ketone functional group;the ring members E, G, J, L and M, which may be identical or different,are each chosen from carbon, oxygen, sulphur and nitrogen atoms andform, together with the ring nitrogen, a ring chosen from pyridine,pyrimidine, pyrazine, triazine and pyridazine rings; p is an integerranging from 0 to 3; m is an integer ranging from 0 to 5; p+m is aninteger ranging from 0 to 5; R is chosen from halogens, a hydroxylradical, C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkyl radicals, C₂-C₆polyhydroxyalkyl radicals, C₁-C₆ alkoxy radicals,tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, amido radicals, carboxylradicals, C₁-C₆ alkylcarbonyl radicals, thio radicals, C₁-C₆ thioalkylradicals, (C₁-C₆)alkylthio radicals, amino radicals, amino radicalssubstituted with at least one radical chosen from (C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl, amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆monohydroxyalkyl radicals and C₂-C₆ polyhydroxyalkyl radicals; it beingunderstood that the radical R is borne by a carbon atom, R₃ is chosenfrom C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkyl radicals, C₂-C₆polyhydroxyalkyl radicals, tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals,(C₁-C₆)alkoxy(C₁-C₆)alkyl radicals, C₁-C₆ carbamylalkyl radicals,(C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals and benzyl radicals; it beingunderstood that the radical R₃ is borne by a nitrogen atom, R₇ is chosenfrom C₁-C₆ alkyl radicals; C₁-C₆ monohydroxyalkyl radicals; C₂-C₆polyhydroxyalkyl radicals; aryl radicals; benzyl radicals; C₁-C₆aminoalkyl radicals; C₁-C₆ aminoalkyl radicals wherein the amine ismono- or disubstituted with a radical or two radicals, which may beidentical or different, chosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl,amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆ carboxyalkyl radicals;C₁-C₆ carbamylalkyl radicals; C₁-C₆ trifluoroalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals; C₁-C₆ sulphonamidoalkylradicals; (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radicals,N-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylsulphonamido(C₁-C₆)alkyl radicals; x is 0 or 1 when x=0,the linking arm D is attached to the nitrogen atom, when x=1, thelinking arm D is attached to one of the ring members chosen from E, G,J, L and M, and Y is a counter-ion; and a second compartment comprisingat least one oxidizing agent.
 36. A process for the dyeing of keratinfibers, comprising applying to the keratin fibers a dyeing compositioncomprising, in a medium suitable for dyeing, at least one oxidation basechosen from pyrrolidinyl-substituted para-phenylenediamine derivativesof formula (I) and the addition salts thereof

wherein: n ranges from 0 to 4, wherein when n is greater than or equalto 2, then the radicals R₁ may be identical or different, R₁ is chosenfrom halogens; onium radicals Z; and C₁-C₆ aliphatic and alicyclic,saturated and unsaturated hydrocarbon-based chains wherein at least onecarbon atom may be replaced with an entity chosen from an oxygen atom, anitrogen atom, a silicon atom, a sulphur atom, and a SO₂ radical, withthe proviso that the radical R₁ does not comprise a peroxide bond, adiazo radical, a nitro radical or a nitroso radical, R₂ is chosen fromonium radicals Z and radicals —X—C═NR₈—NR₉R₁₀, wherein the X is chosenfrom oxygen and —NR₁₁ radicals; R₈, R₉, R₁₀ and R₁₁, which may beidentical or different, are each chosen from hydrogen, C₁-C₄ alkylradicals and C₁-C₄ hydroxyalkyl radicals; the onium radicals Z arechosen from radicals of formulae (II), (III), and (IV): formula (II):

wherein D is a linking arm chosen from a covalent bond and linear andbranched C₁-C₁₄ alkylene chains which may be interrupted with at leastone hetero atom chosen from oxygen, sulphur and nitrogen, and which maybe substituted with at least one radical chosen from hydroxyl, C₁-C₆alkoxy and amino radicals, and which may bear at least one ketonefunctional group; R₄, R₅ and R₆, which may be identical or different,taken separately, are each chosen from C₁-C₁₅ alkyl radicals; C₁-C₆monohydroxyalkyl radicals; C₂-C₆ polyhydroxyalkyl radicals;(C₁-C₆)alkoxy(C₁-C₆)alkyl radicals; aryl radicals; benzyl radicals;C₁-C₆ amidoalkyl radicals; tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals;C₁-C₆ aminoalkyl radicals; and C₁-C₆ aminoalkyl radicals wherein theamine is mono- or disubstituted with a radical or two radicals, whichmay be identical or different, chosen from C₁-C₄ alkyl,(C₁-C₆)alkylcarbonyl, amido and (C₁-C₆)alkylsulphonyl radicals; with theproviso that when the linking arm D is a covalent bond then R₄ is chosenfrom aryl radicals; benzyl radicals; C₁-C₆ amidoalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals; C₁-C₆ aminoalkyl radicals;and C₁-C₆ aminoalkyl radicals wherein the amine is mono- ordisubstituted with a radical or two radicals, which may be identical ordifferent, chosen from C₁-C₄ alkyl, (C₁-C₆)alkylcarbonyl, amido and(C₁-C₆)alkylsulphonyl radicals, Two of the radicals chosen from R₄, R₅and R₆ form, together with the nitrogen atom to which they are attached,a saturated carbon-based cationic ring chosen from 4-, 5-, 6- and7-membered rings optionally comprising at least one hetero atom, whereinthe cationic ring may be substituted with at least one entity chosenfrom halogens, a hydroxyl radical, C₁-C₆ alkyl radicals, C₁-C₆monohydroxyalkyl radicals, C₂-C₆ polyhydroxyalkyl radicals, C₁-C₆ alkoxyradicals, tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, amido radicals,carboxyl radicals, (C₁-C₆)alkylcarbonyl radicals, thio radicals, C₁-C₆thioalkyl radicals, (C₁-C₆)alkylthio radicals, amino radicals, and aminoradicals mono- di- or tri- substituted with a radical or radicals, whichmay be identical or different, chosen from (C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl, amido and (C₁-C₆)alkylsulphonyl radicals; R₇ ischosen from C₁-C₆ alkyl radicals; C₁-C₆ monohydroxyalkyl radicals; C₂-C₆polyhydroxyalkyl radicals; aryl radicals; benzyl radicals; C₁-C₆aminoalkyl radicals; C₁-C₆ aminoalkyl radicals wherein the amine ismono- or disubstituted with a radical or two radicals, which may beidentical or different, chosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl,amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆ carboxyalkyl radicals;C₁-C₆ carbamylalkyl radicals; C₁-C₆ trifluoroalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals; C₁-C₆ sulphonamidoalkylradicals; (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radicals;N-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylsulphonamido(C₁-C₆)alkyl radicals; x is 0 or 1, when x=0,then the linking arm D is attached to the nitrogen atom bearing theradicals R₄, R₅, and R₆, when x=1, then two of the radicals chosen fromR₄, R₅, and R₆ form, together with the nitrogen atom to which they areattached, a saturated ring chosen from 5-, 6- and 7-membered rings andthe linking arm D is linked to a carbon atom of the saturated ring; andY is a counter-ion; formula (III):

wherein D is a linking arm chosen from a covalent bond and linear andbranched C₁-C₁₄ alkylene chains that may be interrupted with at leastone hetero atom chosen from oxygen, sulphur and nitrogen, and that maybe substituted with at least one radical chosen from hydroxyl, C₁-C₆alkoxy and amino radicals, and that may bear at least one ketonefunctional group; the ring members E, G, J and L, which may be identicalor different, are each chosen from carbon, oxygen, sulphur and nitrogenatoms to form, together with the ring nitrogen, a ring chosen frompyrrole, pyrazole, imidazole, triazole, oxazole, isoxazole, thiazole andisothiazole rings, q is an integer ranging from 0 to 4; o is an integerranging from 0 to 3; q+o is an integer ranging from 0 to 4; R, which maybe identical or different, is chosen from halogens, a hydroxyl radical,C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkyl radicals, C₂-C₆polyhydroxyalkyl radicals, C₁-C₆ alkoxy radicals,tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, amido radicals, carboxylradicals, C₁-C₆ alkylcarbonyl radicals, thio radicals, C₁-C₆ thioalkylradicals, (C₁-C₆)alkylthio radicals, amino radicals, amino radicalsmono- or disubstituted with a radical or two radicals, which may beidentical or different, chosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl,amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆ monohydroxyalkylradicals and C₂-C₆ polyhydroxyalkyl radicals; it being understood thatthe radical R is borne by a carbon atom, R₃, which may be identical ordifferent, is chosen from C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkylradicals, C₂-C₆ polyhydroxyalkyl radicals,tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, (C₁-C₆)alkoxy(C₁-C₆)alkylradicals, C₁-C₆ carbamylalkyl radicals, (C₁-C₆)alkylcarboxy(C₁-C₆)alkylradicals and benzyl radicals; it being understood that the radical R₃ isborne by a nitrogen atom, R₇ is chosen from C₁-C₆ alkyl radicals; C₁-C₆monohydroxyalkyl radicals; C₂-C₆ polyhydroxyalkyl radicals; arylradicals; benzyl radicals; C₁-C₆ aminoalkyl radicals; C₁-C₆ aminoalkylradicals wherein the amine is substituted with at least one radicalchosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl, amido and(C₁-C₆)alkylsulphonyl radicals; C₁-C₆ carboxyalkyl radicals; C₁-C₆carbamylalkyl radicals; C₁-C₆ trifluoroalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals; C₁-C₆ sulphonamidoalkylradicals; (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;N-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylsulphonamido(C₁-C₆)alkyl radicals; x is 0 or 1 when x=0,the linking arm D is attached to the nitrogen atom, when x=1, thelinking arm D is attached to one of the ring members chosen from E, G, Jand L, and Y is a counter-ion; formula (IV):

wherein: D is a linking arm chosen from a covalent bond and linear andbranched C₁-C₁₄ alkylene chains which may be interrupted with at leastone hetero atom chosen from oxygen, sulphur and nitrogen atoms, andwhich may be substituted with at least one hydroxyl, C₁-C₆ alkoxy andamino radicals, and which may bear at least one ketone functional group;the ring members E, G, J, L and M, which may be identical or different,are each chosen from carbon, oxygen, sulphur and nitrogen atoms andform, together with the ring nitrogen, a ring chosen from pyridine,pyrimidine, pyrazine, triazine and pyridazine rings; p is an integerranging from 0 to 3; m is an integer ranging from 0 to 5; p+m is aninteger ranging from 0 to 5; R is chosen from halogens, a hydroxylradical, C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkyl radicals, C₂-C₆polyhydroxyalkyl radicals, C₁-C₆ alkoxy radicals,tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, amido radicals, carboxylradicals, C₁-C₆ alkylcarbonyl radicals, thio radicals, C₁-C₆ thioalkylradicals, (C₁-C₆)alkylthio radicals, amino radicals, amino radicalssubstituted with at least one radical chosen from (C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl, amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆monohydroxyalkyl radicals and C₂-C₆ polyhydroxyalkyl radicals; it beingunderstood that the radical R is borne by a carbon atom, R₃ is chosenfrom C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkyl radicals, C₂-C₆polyhydroxyalkyl radicals, tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals,(C₁-C₆)alkoxy(C₁-C₆)alkyl radicals, C₁-C₆ carbamylalkyl radicals,(C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals and benzyl radicals; it beingunderstood that the radical R₃ is borne by a nitrogen atom, R₇ is chosenfrom C₁-C₆ alkyl radicals; C₁-C₆ monohydroxyalkyl radicals; C₂-C₆polyhydroxyalkyl radicals; aryl radicals; benzyl radicals; C₁-C₆aminoalkyl radicals; C₁-C₆ aminoalkyl radicals wherein the amine ismono- or disubstituted with a radical or two radicals, which may beidentical or different, chosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl,amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆ carboxyalkyl radicals;C₁-C₆ carbamylalkyl radicals; C₁-C₆ trifluoroalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals; C₁-C₆ sulphonamidoalkylradicals; (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radicals;N-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylsulphonamido(C₁-C₆)alkyl radicals; x is 0 or 1 when x=0,the linking arm D is attached to the nitrogen atom, when x=1, thelinking arm D is attached to one of the ring members chosen from E, G,J, L and M, and Y is a counter-ion.
 37. A compound chosen from nitropyrrolidinyl-substituted para-phenylenediamine derivatives of formula(I′) and the addition salts thereof

wherein: n ranges from 0 to 4, wherein when n is greater than or equalto 2, then the radicals R₁ may be identical or different, R₁ is chosenfrom halogens; onium radicals Z; and C₁-C₆ aliphatic and alicyclic,saturated and unsaturated hydrocarbon-based chains wherein at least onecarbon atom may be replaced with an entity chosen from an oxygen atom, anitrogen atom, a silicon atom, a sulphur atom, and a SO₂ radical, withthe proviso that the radical R₁ does not comprise a peroxide bond, adiazo radical, a nitro radical or a nitroso radical, R₂ is chosen fromonium radicals Z and radicals —X—C═NR₈—NR₉R₁₀, wherein the X is chosenfrom oxygen and —NR₁₁ radicals; R₈, R₉, R₁₀ and R₁₁, which may beidentical or different, are each chosen from hydrogen, C₁-C₄ alkylradicals and C₁-C₄ hydroxyalkyl radicals; the onium radicals Z arechosen from radicals of formulae (II), (III), and (IV): formula (II):

wherein D is a linking arm chosen from a covalent bond and linear andbranched C₁-C₁₄ alkylene chains which may be interrupted with at leastone hetero atom chosen from oxygen, sulphur and nitrogen, and which maybe substituted with at least one radical chosen from hydroxyl, C₁-C₆alkoxy and amino radicals, and which may bear at least one ketonefunctional group; R₄, R₅ and R₆, which may be identical or different,taken separately, are each chosen from C₁-C₁₅ alkyl radicals; C₁-C₆monohydroxyalkyl radicals; C₂-C₆ polyhydroxyalkyl radicals;(C₁-C₆)alkoxy(C₁-C₆)alkyl radicals; aryl radicals; benzyl radicals;C₁-C₆ amidoalkyl radicals; tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals;C₁-C₆ aminoalkyl radicals; and C₁-C₆ aminoalkyl radicals wherein theamine is mono- or disubstituted with a radical or two radicals, whichmay be identical or different, chosen from C₁-C₄ alkyl,(C₁-C₆)alkylcarbonyl, amido and (C₁-C₆)alkylsulphonyl radicals; with theproviso that when the linking arm D is a covalent bond then R₄ is chosenfrom aryl radicals; benzyl radicals; C₁-C₆ amidoalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals; C₁-C₆ aminoalkyl radicals;and C₁-C₆ aminoalkyl radicals wherein the amine is mono- ordisubstituted with a radical or two radicals, which may be identical ordifferent, chosen from C₁-C₄ alkyl, (C₁-C₆)alkylcarbonyl, amido and(C₁-C₆)alkylsulphonyl radicals, Two of the radicals chosen from R₄, R₅and R₆ form, together with the nitrogen atom to which they are attached,a saturated carbon-based cationic ring chosen from 4-, 5-, 6- and7-membered rings optionally comprising at least one hetero atom, whereinthe cationic ring may be substituted with at least one entity chosenfrom halogens, a hydroxyl radical, C₁-C₆ alkyl radicals, C₁-C₆monohydroxyalkyl radicals, C₂-C₆ polyhydroxyalkyl radicals, C₁-C₆ alkoxyradicals, tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, amido radicals,carboxyl radicals, (C₁-C₆)alkylcarbonyl radicals, thio radicals, C₁-C₆thioalkyl radicals, (C₁-C₆)alkylthio radicals, amino radicals, and aminoradicals mono- di- or tri- substituted with a radical or radicals, whichmay be identical or different, chosen from (C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl, amido and (C₁-C₆)alkylsulphonyl radicals; R₇ ischosen from C₁-C₆ alkyl radicals; C₁-C₆ monohydroxyalkyl radicals; C₂-C₆polyhydroxyalkyl radicals; aryl radicals; benzyl radicals; C₁-C₆aminoalkyl radicals; C₁-C₆ aminoalkyl radicals wherein the amine ismono- or disubstituted with a radical or two radicals, which may beidentical or different, chosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl,amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆ carboxyalkyl radicals;C₁-C₆ carbamylalkyl radicals; C₁-C₆ trifluoroalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals; C₁-C₆ sulphonamidoalkylradicals; (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radicals;N-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylsulphonamido(C₁-C₆)alkyl radicals; x is 0 or 1, when x=0,then the linking arm D is attached to the nitrogen atom bearing theradicals R₄, R₅, and R₆, when x=1, then two of the radicals chosen fromR₄, R₅, and R₆ form, together with the nitrogen atom to which they areattached, a saturated ring chosen from 5-, 6- and 7-membered rings andthe linking arm D is linked to a carbon atom of the saturated ring; andY is a counter-ion; formula (III):

wherein D is a inking arm chosen from a covalent bond and linear andbranched C₁-C₁₄ alkylene chains that may be interrupted with at leastone hetero atom chosen from oxygen, sulphur and nitrogen, and that maybe substituted with at least one radical chosen from hydroxyl, C₁-C₆alkoxy and amino radicals, and that may bear at least one ketonefunctional group; the ring members E, G, J and L, which may be identicalor different, are each chosen from carbon, oxygen, sulphur and nitrogenatoms to form, together with the ring nitrogen, a ring chosen frompyrrole, pyrazole, imidazole, triazole, oxazole, isoxazole, thiazole andisothiazole rings, q is an integer ranging from 0 to 4; o is an integerranging from 0 to 3; q+o is an integer ranging from 0 to 4; R, which maybe identical or different, is chosen from halogens, a hydroxyl radical,C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkyl radicals, C₂-C₆polyhydroxyalkyl radicals, C₁-C₆ alkoxy radicals,tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, amido radicals, carboxylradicals, C₁-C₆ alkylcarbonyl radicals, thio radicals, C₁-C₆ thioalkylradicals, (C₁-C₆)alkylthio radicals, amino radicals, amino radicalsmono- or disubstituted with a radical or two radicals, which may beidentical or different, chosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl,amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆ monohydroxyalkylradicals and C₂-C₆ polyhydroxyalkyl radicals; it being understood thatthe radical R is borne by a carbon atom, R₃, which may be identical ordifferent, is chosen from C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkylradicals, C₂-C₆ polyhydroxyalkyl radicals,tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, (C₁-C₆)alkoxy(C₁-C₆)alkylradicals, C₁-C₆ carbamylalkyl radicals, (C₁-C₆)alkylcarboxy(C₁-C₆)alkylradicals and benzyl radicals; it being understood that the radical R₃ isborne by a nitrogen atom, R₇ is chosen from C₁-C₆ alkyl radicals; C₁-C₆monohydroxyalkyl radicals; C₂-C₆ polyhydroxyalkyl radicals; arylradicals; benzyl radicals; C₁-C₆ aminoalkyl radicals; C₁-C₆ aminoalkylradicals wherein the amine is substituted with at least one radicalchosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl, amido and(C₁-C₆)alkylsulphonyl radicals; C₁-C₆ carboxyalkyl radicals; C₁-C₆carbamylalkyl radicals; C₁-C₆ trifluoroalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals; C₁-C₆ sulphonamidoalkylradicals; (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;N-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylsulphonamido(C₁-C₆)alkyl radicals; x is 0 or 1 when x=0,the linking arm D is attached to the nitrogen atom, when x=1, thelinking arm D is attached to one of the ring members chosen from E, G, Jand L, and Y is a counter-ion; formula (IV):

wherein: D is a linking arm chosen from a covalent bond and linear andbranched C₁-C₁₄ alkylene chains which may be interrupted with at leastone hetero atom chosen from oxygen, sulphur and nitrogen atoms, andwhich may be substituted with at least one hydroxyl, C₁-C₆ alkoxy andamino radicals, and which may bear at least one ketone functional group;the ring members E, G, J, L and M, which may be identical or different,are each chosen from carbon, oxygen, sulphur and nitrogen atoms andform, together with the ring nitrogen, a ring chosen from pyridine,pyrimidine, pyrazine, triazine and pyridazine rings; p is an integerranging from 0 to 3; m is an integer ranging from 0 to 5; p+m is aninteger ranging from 0 to 5; R is chosen from halogens, a hydroxylradical, C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkyl radicals, C₂-C₆polyhydroxyalkyl radicals, C₁-C₆ alkoxy radicals,tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals, amido radicals, carboxylradicals, C₁-C₆ alkylcarbonyl radicals, thio radicals, C₁-C₆ thioalkylradicals, (C₁-C₆)alkylthio radicals, amino radicals, amino radicalssubstituted with at least one radical chosen from (C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl, amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆monohydroxyalkyl radicals and C₂-C₆ polyhydroxyalkyl radicals; it beingunderstood that the radical R is borne by a carbon atom, R₃ is chosenfrom C₁-C₆ alkyl radicals, C₁-C₆ monohydroxyalkyl radicals, C₂-C₆polyhydroxyalkyl radicals, tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals,(C₁-C₆)alkoxy(C₁-C₆)alkyl radicals, C₁-C₆ carbamylalkyl radicals,(C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals and benzyl radicals; it beingunderstood that the radical R₃ is borne by a nitrogen atom, R₇ is chosenfrom C₁-C₆ alkyl radicals; C₁-C₆ monohydroxyalkyl radicals; C₂-C₆polyhydroxyalkyl radicals; aryl radicals; benzyl radicals; C₁-C₆aminoalkyl radicals; C₁-C₆ aminoalkyl radicals wherein the amine ismono- or disubstituted with a radical or two radicals, which may beidentical or different, chosen from (C₁-C₆)alkyl, (C₁-C₆)alkylcarbonyl,amido and (C₁-C₆)alkylsulphonyl radicals; C₁-C₆ carboxyalkyl radicals;C₁-C₆ carbamylalkyl radicals; C₁-C₆ trifluoroalkyl radicals;tri(C₁-C₆)alkylsilane(C₁-C₆)alkyl radicals; C₁-C₆ sulphonamidoalkylradicals; (C₁-C₆)alkylcarboxy(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphinyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylsulphonyl(C₁-C₆)alkyl radicals;(C₁-C₆)alkylcarbonyl(C₁-C₆)alkyl radicals;N-(C₁-C₆)alkylcarbamyl(C₁-C₆)alkyl radicals; andN-(C₁-C₆)alkylsulphonamido(C₁-C₆)alkyl radicals; x is 0 or 1 when x=0,the linking arm D is attached to the nitrogen atom, when x=1, thelinking arm D is attached to one of the ring members chosen from E, G,J, L and M, and Y is a counter-ion.